INTERNATIONAL UNION OF PURE AND APPLIED CHEMISTRY

ORGANIC CHEMISTRY DIVISION

Commission on Nomenclature of Organic Chemistry

REVISION OF THE EXTENDED

HANTZSCH-WIDMAN SYSTEM OF
NOMENCLATURE FOR
HETEROMONOCYCLES
(Recommendations 1982)

Prepared for publication by W. H. Powell and published in Pure Appl. Chem., 1983, 55,
409-416.

http://www.chem.qmul.ac.uk/iupac/hetero/HW.html

World Wide Web version Prepared by G. P. Moss

Department of Chemistry, Queen Mary University of London,

Mile End Road, London, E1 4NS, UK
[email protected]

These Rules are as close as possible to the published version [see W. H. Powell Pure
Appl. Chem., 1983, 55, 409-416. Copyright IUPAC; reproduced with the permission of
IUPAC]. If you need to cite these rules please quote this reference as their source.

See also Can. J. Chem., 1989, 67(6), v-viii (in French); Helv. Chim. Acta, 1990, 73,
1518-1523 (in French); Mag. Kem. Foly., 1988, 94, 291-310 (in Hungarian); Wiad.
Chem., 1989, 43, 85-92 (in Polish) and Ann. Quim., 1992, 88, 590-595 (in Spanish).

For problems in converting the text into a World Wide Web version see the IUPAC
home page.

Any comments, corrections or suggestions for a future edition should be e-mailed to

[email protected]

Contents

INTRODUCTION

Introduction
Discussion
Conclusions
RULES RB-1.1 and TABLES 1 and 2.
Recommendations
RB-1.1 Saturated Monocyclic with no more than Five Membered Rings with Nitrogen
Atom(s)
Table I Prefixes for the Hantzsch-Widman System
Table II Stems for the Hantzsch-Widman System
RULES RB-1.2 to RB-1.5.
RB-1.2 Monocycle with up to ten ring members, one of which is a heteroatom
RB-1.3 Two or more atoms of the same heteroatom
RB-1.4 Two or more different heteroatoms
RB-1.5 Heteromonocycle with less than the maximum number of noncumulative double
bonds
REFERENCES

REVISION OF THE EXTENDED HANTZSCH-WIDMAN SYSTEM

OF NOMENCLATURE FOR HETEROMONOCYCLES

(Recommendations 1982)

Note. These recommendations replace entirely Rule B-1. Extension of the Hantzsch-
Widman System, in Section B: Fundamental Heterocyclic Systems, of the IUPAC Rules
for Nomenclature of Organic Chemistry (ref. 1a).

Contents

Introduction
Discussion
Conclusions
References for this section

Continued with Rule RB-1.1 and Tables 1 and 2.

INTRODUCTION

In 1887 and 1888, Hantzsch (ref. 2) and Widman (ref. 3) independently introduced
methods for naming five- and six-membered nitrogen monocycles. Although differing
in details, such as expressing the order of the heteroatoms and indicating their positions
in the ring, both methods were based on the same underlying principle, i.e., the
combination of appropriate prefixes, representing heteroatoms, with stems, representing
the size of the ring. At first, only the heteroatoms oxygen, sulfur, and selenium, in
addition to nitrogen, and the stems -ol (-ole) and -in (-ine) denoting five- and six-
membered rings, respectively, were used. Although these initial proposals underwent
the usual discussion, refinement, and inevitable modification, the basic principle
survived (ref. 4).

The system was extended to include rings of other sizes, additional heteroatoms, and the
expression of various levels of hydrogenation (refs. 5 and 6) and eventually was
documented by Patterson and Capell in 1940 as a systematic method for naming
heteromonocycles (ref. 7). Stems were provided for all the various levels of
hydrogenation for three-, four-, and five-membered rings, but for the six- through ten-
membered rings stems were provided only for the completely unsaturated rings and the
completely saturated rings without nitrogen atoms. The type of heteroatom to which the
system was applicable was apparently not limited; the first edition of The Ring Index
(ref. 7) contains examples of heteromonocycles with the metallic heteroatoms Bi, Ge,
Sn, Pb, Zn, Hg, and Cu as well as many nonmetallic heteroatoms.

In 1957, the IUPAC Commission on Nomenclature of Organic Chemistry codified this

extension of the Hantzsch-Widman system as part of its rules for the nomenclature of
organic chemistry (ref. 8a). The heteroatoms to which the system applied were specified
and certain exceptions and modifications were noted in order to avoid formation of
names identical with some already in use for entirely different compounds.

DISCUSSION

Since the l957 Rules, the only heteroatom added to the system was boron, first
mentioned in a comment to the Rules (ref. 9) and included officially in the third edition
of Sections A and B of the Organic Nomenclature Rules (ref. 10a). However, exceptions
and modifications to the system were added in both the third edition (ref. 10b) and the
fourth edition (ref. 1b) of Sections A and B. The exceptions and modifications all
involve six-membered heteromonocycles and are summarized below.

1. Names for saturated six-membered rings without nitrogen, but containing silicon,
germanium, tin, or lead, are excluded (ref. 1c) because of names such as silane and
disilane for acyclic hydrides (refs. 11 and 12). Although the same problem occurs with
the analogous boron rings, they were not excluded; instead the stem "-inane" was used
in place of "-ane" (ref. 1d). Although not codified in the IUPAC Organic Nomenclature
Rules, this stem change and modified prefixes such as "germana-" rather than "germa-",
have been used to avoid this problem with other saturated six-membered rings (refs. 7
and 13).

2. Names for six-membered rings that contain phosphorus , arsenic, or antimony require
a change in the prefix for denoting the heteroatom because of names such as arsine and
diphosphine for acyclic hydrides (ref. 1e). These prefix modifications were fully
documented for the unsaturated rings in the 1957 Organic Rules (ref. 8b), but their use
for saturated rings was noted only in the third edition of the Sections A and B Rules
(ref. 10c). Even a modified prefix is not enough for saturated six-membered phosphorus
rings; the stem "-inane" instead of "-ane" is also needed to avoid the name phosphorane
used for PH (ref. 1d). (See Note)
5

Note. In the fourth edition of the Section B Organic Rules (ref. 1a) the prefix for
bismuth was changed to bisma-, as it had been in the first and second editions of Section
B (refs. 8b and 8c), thus removing the need for an exception for bismuth rings in order
to avoid the same problem for six-membered bismuth rings as noted here for the
corresponding phosphorus, arsenic, and antimony rings.

In addition to the problems noted above in naming six-membered rings according to the
present rules, a number of other comments on the system have been made over the
years, including the following:
1. Stems should be provided for saturated rings containing nitrogen with more than six
ring members.

2. The system should be extended beyond ten-membered rings.

3. The halogen elements should be included since the system has been applied for
naming rings containing cationic halogen ring atoms.

4. Other metallic elements should be included.

5. The numbering rules should be completely consistent with those for numbering
heteroatoms in polycyclic ring systems.

CONCLUSIONS

Although the Hantzsch-Widman system for naming heteromonocycles as currently

documented (ref. 1a) has some complications and defects, as noted above, it does have
distinct advantages and is widely used, not onlv for naming heteromonocycles, but also
for describing heteromonocyclic components in naming fused heterocyclic systems.
Therefore, the IUPAC Commission on Nomenclature of Organic Chemistry decided
that a revision of the svstem was justified and would be useful, and prepared provisional
recommendations for such a revision (ref. 14). On the basis of the comments received
on the provisional recommendations, the Commission now presents the following
recommendations. The main points may be summarized briefly as follows:

1. The stems for three-membered rings containing nitrogen and for saturated four- and
five-membered rings containing nitrogen are retained. The use of the stems "-inine" and
"-inane" to name six-membered rings where the stems "-ine" and "-ane" would be
ambiguous has been carefully delineated. All other heteromonocycles containing no
more than ten ring members are named by a single set of endings for each ring size.

2. The special terminations for four- and five-membered rings containing one double
bond when two double bonds are possible (ref. 1f) are no longer recommended.

3. The number of elements covered by the system is increased to nineteen by including

the halogen elements needed for naming heterocyclic rings containing halogen ring
members.

4. The numbering rules in the present Hantzsch-Widman rules (ref. 1g) are retained.

5. The subtractive prefix "dehydro" (see ref. 15a) is introduced as an alternative to the
additive prefix "hydro" (see ref. 15b) for naming unsaturated heteromonocycles having
less than the maximum number of noncumulative double bonds.

REFERENCES

1. International Union of Pure and Applied Chemistry, Nomenclature of Organic

Chemistry, Sections A, B, C, D, E, F, and H, 1979 edition, Pergamon Press, Oxford,
1979: [a] p. 53-54; [b] Rule B-1.1, Tables I and II, footnotes, p. 53; [c] Rule B-1.1,
Table II, footnote (d), p. 53; [d] Rule B-1.1, Table I, footnote, p. 53; [e] Rule B-1.1,
Table I, footnote, and Table II, footnote (b), p. 53; [f] Rule B-1.2, exception, p. 54; [g]
Rules 1.51, p. 55; [h] pp. 55-63; [i] p.68.

2. A. Hantzsch and J. H. Weber, Ber. Dtsch. Chem. Ges., 20, 3118-3132 (1887).

3. O. Widman, J. Prakt. Chem., 38, 185-201 (1888)

4. See, for example, F. Beilstein, Handbuch der Organischen Chemie, 3rd. ed., Vol. 4,
Leopold Voss, Hamburg, 1899, pp. 1-2.

5. W. H. Hale, J. Am. Chem. Soc., 41, 370-378 (1919).

6. A. M. Patterson, J. Am. Chem. Soc., 50, 3074-7078 (1938).

7. A. M. Patterson and L. I. Capell, The Ring Index, Reinhold, New York, 1940, pp. 20-
21.

8. International Union of Pure and Applied Chemistry, Nomenclature of Organic

Chemistry (1957), Sections A and B, 1st ed., Butterworths, London, 1958: [a] Rule B-1,
pp. 51-53; [b] Rule B-1.1, Table I, p. 51; [c] 2nd ed., Butterworths, London, 1966,
Table I, p. 51.

9. International Union of Pure and Applied Chemistry, Definitive Rules of Organic

Chemistry, J. Am. Chem. Soc., 82, 5545-5574 (1960), Comment to Table I, p. 5566.

10. International Union of Pure and Applied Chemistry, Nomenclature of Organic

Chemistry, Sections A and B, 3rd ed. and Section C, 2nd ed., Butterworths, London,
1971: [a] Rule B-1.1, Table 1, p. 53; [b] Rule B-1.1, Tables I and II, footnotes, p. 53; [c]
Rule B-1.1, Table I, footnote, p. 53.

11. International Union of Pure and Applied Chemistry, Nomenclature of Organosilicon

Compounds, Compt. Rend. Quinziène Conf., Amsterdam, 1949, pp. 127-132.

12. American Chemical Society, Report of the ACS Nomenclature, Spelling and
Pronunciation Committee for the First Half of 1952. F. Organosilicon Compounds,
Chem. Eng. News, 30, 4517-4522 (1952).

13. A. M. Patterson, L. T. Capell, and D. F. Walker, The Ring Index, 2nd ed., American
Chemical Society, Washington, D.C., 1960; Supplement I, 1963; Supplement II, 1964;
Supplement III, 1965.

14. International Union of Pure and Applied Chemistry, Revision of the Extended
Hantzsch-Widman System of Nomenclature for Heteromonocycles, Provisional
Recommendations, 1978, Pure Appl. Chem., 51, 1995-2003 (1979).

15. Reference 1, Section C: [a] Rule C-41.2, p. 115; [b] Rule C-32.1, p. 114; [c]
Preamble, Elision of Vowels, p. 83; [d] Rule C-923.1, p. 289; [e] Rule C-13.11(e),
footnote, p. 99; [f] pp. 108, 115-116.
Continued with Rule RB-1.1 and Tables 1 and 2.

Return to Hantzsch-Widman home page.

Revision of the extended Hantzsch-Widman system of nomenclature for

heteromonocycles
(Recommendations 1982)

Rule RB-1.1 and Tables 1 and 2

Contents

Recommendations
RB-1.1 Saturated Monocyclic with no more than Five Membered Rings with Nitrogen
Atom(s)
Table I Prefixes for the Hantzsch-Widman System
Table II Stems for the Hantzsch-Widman System
References for this section

Continued with Rules RB-1.2 to RB-1.5.

RECOMMENDATIONS

The following recommendations, designated in this report as RB (from Revision of the

B rules), are a revision of the rules given under Rule B-1 of the 1979 edition of the
IUPAC Rules of Nomenclature of Organic Chemistry (ref. 1a) and replace them in their
entirety.

This revision is intended to provide a system for naming all heteromonocycles having
no more than ten ring members in which the heteroatoms are in defined standard
valence states (see Note).

Note. A defined valence state is required for the unambiguous application of the
principle of maximum number of noncumulative double bonds.

Obviously the system could easily accommodate all elements, if a defined valence state
has been accepted. However, it should be extended only with necessary caution to avoid
confusion with existing terminology.

These recommendations are not intended to supersede commonly used trivial names,
such as thiophene, furan, pyrrole, pyridine, and morpholine, that are recognized under
Rule B-2 (ref 1h); but do supersede those names for partially saturated
heteromonocycles requiring special terminations as given by Rule B-1.2 (ref. 1f).

Heteromonocycles with more than ten ring members are named by replacement
nomenclature as described by Rule B-4.1 (ref. 1i).
RB-1.1. Saturated Monocyclic with no more than Five Membered Rings with
Nitrogen Atom(s)

(Replaces Rules B-1.1, in part, and B-1.51).

A saturated monocycle with no more than five ring members, and having only a single
nitrogen atom, is named by adding the prefix "aza-" (see Table I) with elision of the
final "a" of the prefix (see Note) to a stem "-iridine", "-etidine", or "-olidine" according
to whether the ring has three, four, or five ring members, respectively. The numbering
begins with the nitrogen atom.

Note. In organic replacement nomenclature the final "a" of the replacement prefix is not
elided (ref. 15c).

Two or more nitrogen atoms are denoted by appropriate numerical prefixes (see RB-
1.3).

Other heteroatoms in addition to nitrogen atoms are indicated by appropriate prefixes

from Table I. The order of citation of the prefixes and the numbering of the
heteromonocycle follow the principles in RB-1.4.

Examples:

1. Aziridine

2. 1,3-Diazetidine

3. 1,3,2-Diazarsetidine

4. 1,4,2-Oxazaphospholidine

Note: This recommendation is not intended to supersede trivial names recognized under
Rule B-2 (Ref. 1h), such as pyrrolidine or imidazolidine

Table I: Prefixes for the Hantzsch-Widman System

Element Valence Prefix Element Valence Prefix

Fluorine I Fluora Arsenic III Arsa

Chlorine I Chlora Antimony III Stiba
Bromine I Broma Bismuth III Bisma
Iodine I Ioda Silicon IV Sila
Oxygen II Oxa Germanium IV Germa
Sulfur II Thia Tin IV Stanna
 Selenium II Selena Lead IV Plumba
Tellurium II Tellura Boron III Bora
Nitrogen III Aza Mercury II Mercura
Phosphorus III Phospha
Note. Prefixes for the halogen elements are included in order to provide for naming
heteromonocycles containing cationic halogen atoms (to be described in a later report)
and halogen atoms in nonstandard valence states (ref. 17).

Table II Stems for the Hantzsch-Widman System (see Notes 1, 2 and 3)

The stem for six-membered rings depends on the least preferred heteroatom in the ring
(see RB-1.4), i.e., the heteroatom whose name directIy precedes the stem.

To determine the proper stem for six-membered rings, select the set below that contains
the least preferred heteroatom before consulting the table. For example, the proper stem
for the dioxazine ring is found after set 6B, which contains the element nitrogen.

6A O4, S, Se, Te, Bi, Hg

6B N5, Si, Ge, Sn, Pb

6C B, F, Cl, Br, I, P, As, Sb

Ring size Unsaturated Saturated Ring size Unsaturated

Saturated
(Note 6) (Note 7) (Note 6)
(Note 7)
3 irene (Note 8) irane (Note 9) 7 epine
epane
4 ete etane (Note 9) 8 ocine
ocane
5 ole olane (Note 9) 9 onine
onane
6A ine (Note 4) ane 10 ecine
ecane
6B ine (Note 5) inane
6C inine inane
Note 1. A terminal "e" is used on all stems in these recommendations but is optional.

Note 2. The stems for ring sizes 3, 4, 7, 8, 9, and 10 may be considered to be derived
from numerical prefixes as follows: "ir" from tri, "et" from tetra, "ep" from hepta, "oc"
from octa, "on" from nona, and "ec" from deca.

Note 3. The stems "etine" and "oline", which would be consistent with the other stems
for unsaturated rings, cannot be used because they were formerly used to name four-
and five-membered rings containing nitrogen, respectively, having only one of two
possible double bonds (ref. 1f).

Note 4. Oxine should not be used for pyran because it is used as a trivial name for 8-
quinol

Note 5. Azine cannot be used for pyridine because of its long established use as a class
name for =N-N= compounds (ref. 15d).
Note 6. Used when the ring contains the maximum number of noncumulative double
bonds and at least one double bond is present when the heteroatoms have the valences
given in Table I (see also Note 7).

Note 7. Used when no double bonds are present or when none are possible.

Note 8. The traditional stem "irine" may be used for rings containing nitrogen only.

Note 9. The traditional stems "iridine", ''etidine", and "olidine" are preferred for rings
containing nitrogen and are codified in RB-l.l.

REFERENCES

1. International Union of Pure and Applied Chemistry, Nomenclature of Organic

Chemistry, Sections A, B, C, D, E, F, and H, 1979 edition, Pergamon Press, Oxford,
1979: [a] p. 53-54; [b] Rule B-1.1, Tables I and II, footnotes, p. 53; [c] Rule B-1.1,
Table II, footnote (d), p. 53; [d] Rule B-1.1, Table I, footnote, p. 53; [e] Rule B-1.1,
Table I, footnote, and Table II, footnote (b), p. 53; [f] Rule B-1.2, exception, p. 54; [g]
Rules 1.51, p. 55; [h] pp. 55-63; [i] p.68.

15. Reference 1, Section C: [a] Rule C-41.2, p. 115; [b] Rule C-32.1, p. 114; [c]
Preamble, Elision of Vowels, p. 83; [d] Rule C-923.1, p. 289; [e] Rule C-13.11(e),
footnote, p. 99; [f] pp. 108, 115-116.

17. International Union of Pure and Applied Chemistry, The Designation of

Nonstandard Classical Valence Bondlng in Organic Nomenclature (Provisional), Pure
Appl. Chem., 54, 217-227 (1982). Now published as: Treatment of Variable Valency in
Organic Nomenclature (Lambda Convention) (Recommendations 1983), Pure Appl.
Chem., 56, 769-778 (1984).

Continued with Rules RB-1.2 to RB-1.5.

Return to Hantzsch-Widman home page.

Revision of the extended Hantzsch-Widman system of nomenclature for

heteromonocycles
(Recommendations 1982)

Rules RB-1.2 to RB-1.5

Contents

RB-1.2 Monocycle with up to ten ring members, one of which is a heteroatom

RB-1.3 Two or more atoms of the same heteroatom
RB-1.4 Two or more different heteroatoms
RB-1.5 Heteromonocycle with less than the maximum number of noncumulative double
bonds
References for this section

RB-1.2. Monocycle with up to ten ring members, one of which is a heteroatom.

(Replaces Rules B-1.1, in part, and B-1.51).

A monocycle with no more than ten ring members, one of which is a heteroatom given
in Table I, is named by combining the appropriate prefix from Table I with a stem from
Table II, except as provided by RB-1.1, with elision of the final "a" of the prefix, when
followed by a vowel (see Note).

Note In organic replacement nomenclature the final "a" of the replacement prefix is not
elided (ref. 15c).

The presence of at least one hydrogen atom on a ring atom joined to adjacent ring atoms
by only single bonds in an unsaturated monocycle containing the maximum number of
noncumulative double bonds is denoted by the technique used for indicated hydrogen
(see examples 2 and 4 below) (ref. 16).

The numbering of the heterocycle begins with the heteroatom. Thereafter indicated
hydrogen takes precedence for low locants.

Examples:

1. Oxirane

2. 1H-Azirene [1H-Azirine (traditional)]

3. Azete

4. 2H-Phosphole

5. Silolane

6. Phosphinine (formerly Phosphorin)

7. Borinane

8. Thiepine

9. Azocane (formerly Octahydroazocine)

RB-1.3. Two or more atoms of the same heteroatom

(Replaces Rules B-1.3 and B-1.52).

Two or more heteroatoms of the same element in a heteromonocycle are indicated by

adding an appropriate numerical prefix, such as "di", "tri", etc., to the prefix for the
heteroatom (Table 1). A final "a" of a numerical prefix is elided when followed by a
vowel.

The positions of the heteroatoms are given by numerical locants cited in front of the
name. Numbering begins at a heteroatom and proceeds in the direction that gives the
lowest set of locants to the heteroatoms (see Note a).

Note (a). The lowest set of locants is that series which contains the lowest number at the
first point of difference when two or more series containing the same number of terms
are compared term by term (ref. 15e).

Note (b). Designation of hydrogen atoms bv the technique of indicated hydrogen (see
RB-1.2) at ring positions between two bivalent ring atoms may be omitted.

Examples:

1. 1,3-Dithiolane (the locant set 1,3 is lower than 1,4)

2. 1,3,5,7-Tetroxocane

3. 2H,4H-1,3-Dioxine
(may be written as 4H-1,3-Dioxine; indication of the hydrogen atom at position 2 may
be omitted as explained in the Note (b) to this rule)

4. 1,2,4-Triazine (the locant set 1,2,4 is lower than 1,2,5; 1,3,4; or 1,4,5)

5. 4H-1,3-Diphosphepine (heteroatoms are preferred to indicated hydrogen for

lowest locants)

RB-1.4. Two or more different heteroatoms

(Replaces Rules B-1.4 and B-1.53).

A heteromonocycle with two or more different heteroatoms is named by adding the

appropriate prefix for each heteroatom (Table I) together with a numerical prefix as
prescribed by RB-1.3 if needed, in the order of appearance of the heteroatoms in Table I
(see Note) to an appropre stem (RB-1.1 or RB-1.2). The final "a" of a numerical prefix
is elided when followed by a vowel.

Noteiat. This order of citation follows the element sequence now accepted in the rules of
both inorganic (ref. 18) and organic (ref. 19) nomenclature.

The positions of the heteroatoms are indicated by numerical locants, all of which are
cited before the first heteroatom prefix and in the same order as the heteroatom prefixes
to which they refer.

Numbering of the heteromonocycle begins with a heteroatom whose prefix occurs

earliest in Table I. If there is any choice the numbering should give the lowest set of
locants (see Note (a) to Rule RB-1.3) first to all heteroatoms, then to heteroatoms in the
order of their prefixes.

Examples:

1. 1,3-Oxathiolane (the locant set 1,3 is lower than 1,4)

2. 6H-1,2,5-Thiadiazine (preferred)

(the numbering begins with the sulfur atom, and then the locant set 1,2,5 is lower than
1,3,6)
3. 1,2,4,3-Triazasilolidine

Note that numbering beginning with either nitrogen atom adjacent to the single carbon
atom results in the same lowest locant set, 1,2,3,4, for the four heteroatoms taken as a
complete set without regard to priority. The direction for numbering thus depends on
the comparison of these two lccant sets in the order that the heteroatoms to which they
refer are cited, namely, 1,3,4,2 and 1,2,4,3; the latter set has the lower second locant and
is therefore preferred.

RB-1.5 Heteromonocycle with less than the maximum number of noncumulative

double bonds

(Replaces Rule B-1.2) (see Note).

Note. Thus, the special terminations for partially saturated heteromonocycles as given
by Rule B-1.2 (ref. 1f) are no longer recommended.

A heteromonocycle containing fewer than the maximum number of noncumulative

double bonds may be named by: (a) adding the prefixes "dihydro", "tetrahydro", etc., to
a parent name that indicates the presence of the maximum number of noncumulative
double bonds; or (b) adding the prefixes "didehydro", "tetradehydro", etc., to a parent
name that indicates a fully saturated structure, according to the requirements of Rules C-
16.1 and C-41.2 (ref. 15f). Method (a) is usually preferred.

Heteroatoms and indicated hydrogen have preference over hydro and dehydro prefixes
for determining the beginning and direction of numbering.

Note: The final "o" of a hydro or dehydro prefix is not elided before a following vowel.

Examples:

1. (a) 1,2-Dihydroazete (b) 2,3-Didehydroazetidine (formerly 2

-Azetine or 2-
Azetine)

2. (a) 3,6-Dihydro-2H-phosphepine (b) 1,2,4,5-Tetradehydrophosphepane

3. (a) 2,3,4,7,8,9-Hexahydrooxonine (b) 5,6-Didehydrooxonane

REFERENCES
1. International Union of Pure and Applied Chemistry, Nomenclature of Organic
Chemistry, Sections A, B, C, D, E, F, and H, 1979 edition, Pergamon Press, Oxford,
1979: [a] p. 53-54; [b] Rule B-1.1, Tables I and II, footnotes, p. 53; [c] Rule B-1.1,
Table II, footnote (d), p. 53; [d] Rule B-1.1, Table I, footnote, p. 53; [e] Rule B-1.1,
Table I, footnote, and Table II, footnote (b), p. 53; [f] Rule B-1.2, exception, p. 54; [g]
Rules 1.51, p. 55; [h] pp. 55-63; [i] p.68.

15. Reference 1, Section C: [a] Rule C-41.2, p. 115; [b] Rule C-32.1, p. 114; [c]
Preamble, Elision of Vowels, p. 83; [d] Rule C-923.1, p. 289; [e] Rule C-13.11(e),
footnote, p. 99; [f] pp. 108, 115-116.

16. Reference 1, Section A, Rule A-21.6, p. 25.

17. International Union of Pure and Applied Chemistry, The Designation of

Nonstandard Classical Valence Bonding in Organic Nomenclature (Provisional), Pure
Appl. Chem., 54, 217-227 (1982). Revised version now published as: Treatment of
Variable Valency in Organic Nomenclature (Lambda Convention) (Recommendations
1983), Pure Appl. Chem., 56, 769-778 (1984).

18. International Union of Pure and Applied Chemistry, Nomenclature of Inorganic

Chemistry (1970), 2nd ed., Butterworths, London, 1971, Table IV, p. 104.

19. Reference 1, Section D, Appendix, Table I, pp. 459-460.

Continued with References

Return to Hantzsch-Widman home page.

Revision of the extended Hantzsch-Widman system of nomenclature for

heteromonocycles
(Recommendations 1982)

REFERENCES
1. International Union of Pure and Applied Chemistry, Nomenclature of Organic
Chemistry, Sections A, B, C, D, E, F, and H, 1979 edition, Pergamon Press, Oxford,
1979: [a] p. 53-54; [b] Rule B-1.1, Tables I and II, footnotes, p. 53; [c] Rule B-1.1,
Table II, footnote (d), p. 53; [d] Rule B-1.1, Table I, footnote, p. 53; [e] Rule B-1.1,
Table I, footnote, and Table II, footnote (b), p. 53; [f] Rule B-1.2, exception, p. 54; [g]
Rules 1.51, p. 55; [h] pp. 55-63; [i] p.68.

2. A. Hantzsch and J. H. Weber, Ber. Dtsch. Chem. Ges., 20, 3118-3132 (1887).

3. O. Widman, J. Prakt. Chem., 38, 185-201 (1888)

4. See, for example, F. Beilstein, Handbuch der Organischen Chemie, 3rd. ed., Vol. 4,
Leopold Voss, Hamburg, 1899, pp. 1-2.
5. W. H. Hale, J. Am. Chem. Soc., 41, 370-378 (1919).

6. A. M. Patterson, J. Am. Chem. Soc., 50, 3074-7078 (1938).

7. A. M. Patterson and L. I. Capell, The Ring Index, Reinhold, New York, 1940, pp. 20-
21.

8. International Union of Pure and Applied Chemistry, Nomenclature of Organic

Chemistry (1957), Sections A and B, 1st ed., Butterworths, London, 1958: [a] Rule B-1,
pp. 51-53; [b] Rule B-1.1, Table I, p. 51; [c] 2nd ed., Butterworths, London, 1966,
Table I, p. 51.

9. International Union of Pure and Applied Chemistry, Definitive Rules of Organic

Chemistry, J. Am. Chem. Soc., 82, 5545-5574 (1960), Comment to Table I, p. 5566.

10. International Union of Pure and Applied Chemistry, Nomenclature of Organic

Chemistry, Sections A and B, 3rd ed. and Section C, 2nd ed., Butterworths, London,
1971: [a] Rule B-1.1, Table 1, p. 53; [b] Rule B-1.1, Tables I and II, footnotes, p. 53; [c]
Rule B-1.1, Table I, footnote, p. 53.

11. International Union of Pure and Applied Chemistry, Nomenclature of Organosilicon

Compounds, Compt. Rend. Quinziène Conf., Amsterdam, 1949, pp. 127-132.

12. American Chemical Society, Report of the ACS Nomenclature, Spelling and
Pronunciation Committee for the First Half of 1952. F. Organosilicon Compounds,
Chem. Eng. News, 30, 4517-4522 (1952).

13. A. M. Patterson, L. T. Capell, and D. F. Walker, The Ring Index, 2nd ed., American
Chemical Society, Washington, D.C., 1960; Supplement I, 1963; Supplement II, 1964;
Supplement III, 1965.

14. International Union of Pure and Applied Chemistry, Revision of the Extended
Hantzsch-Widman System of Nomenclature for Heteromonocycles, Provisional
Recommendations, 1978, Pure Appl. Chem., 51, 1995-2003 (1979).

15. Reference 1, Section C: [a] Rule C-41.2, p. 115; [b] Rule C-32.1, p. 114; [c]
Preamble, Elision of Vowels, p. 83; [d] Rule C-923.1, p. 289; [e] Rule C-13.11(e),
footnote, p. 99; [f] pp. 108, 115-116.

16. Reference 1, Section A, Rule A-21.6, p. 25.

17. International Union of Pure and Applied Chemistry, The Designation of

Nonstandard Classical Valence Bonding in Organic Nomenclature (Provisional), Pure
Appl. Chem., 54, 217-227 (1982). Revised version now published as: Treatment of
Variable Valency in Organic Nomenclature (Lambda Convention) (Recommendations
1983), Pure Appl. Chem., 56, 769-778 (1984).

18. International Union of Pure and Applied Chemistry, Nomenclature of Inorganic

Chemistry (1970), 2nd ed., Butterworths, London, 1971, Table IV, p. 104.
19. Reference 1, Section D, Appendix, Table I, pp. 459-460.

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