The molecular geometries of some cyclic nitramines in the gas phase

Igor F. Shishkov, Lev V. Vilkov, M. Kolonits, Béla Rozsondai

Research output: Contribution to journalArticle

41 Citations (Scopus)

Abstract

The structural parameters of 1,3,5-trinitro-1,3,5-triazacyclohexane (RDX), (CH2NNO2)3, 1,3-dinitro-1,3-diazacyclopentane (DDCP), CH2(CH2NNO2)2, and N-nitropyrrolidine (NP), (CH2)4NNO2, have been determined by electron diffraction. The six-membered ring of RDX has a chair form with axial positions of the nitro groups and close to planar bond geometry of the amine nitrogen atoms. The overall C3 symmetry of the molecule is in agreement with the experimental data. The conformation of the five-membered ring in DDCP is a half-chair of C2 symmetry, while that in NP is an envelope of CS symmetry. The nitro groups are in equatorial positions in both molecules. The conformations of pyrrolidine and imidazolidine cycles show interesting features. The pyramidal geometry of the amine nitrogen atom bonds flattens in going from pyrrolidine and N-chloropyrrolidine to NP and DDCP and then to RDX and to dimethylnitramine (DMNA), (CH3)2NNO2.

Original languageEnglish
Pages (from-to)57-64
Number of pages8
JournalStructural Chemistry
Volume2
Issue number1
DOIs
Publication statusPublished - Jan 1991

Fingerprint

RDX
Gases
vapor phases
nitrogen atoms
seats
Geometry
amines
symmetry
geometry
Amines
Conformations
Nitrogen
Imidazolidines
rings
Atoms
Molecules
molecules
envelopes
electron diffraction
Electron diffraction

ASJC Scopus subject areas

  • Chemistry(all)
  • Structural Biology

Cite this

The molecular geometries of some cyclic nitramines in the gas phase. / Shishkov, Igor F.; Vilkov, Lev V.; Kolonits, M.; Rozsondai, Béla.

In: Structural Chemistry, Vol. 2, No. 1, 01.1991, p. 57-64.

Research output: Contribution to journalArticle

Shishkov, Igor F. ; Vilkov, Lev V. ; Kolonits, M. ; Rozsondai, Béla. / The molecular geometries of some cyclic nitramines in the gas phase. In: Structural Chemistry. 1991 ; Vol. 2, No. 1. pp. 57-64.
@article{776d421e77ea40fbb0822f6451c31e7d,
title = "The molecular geometries of some cyclic nitramines in the gas phase",
abstract = "The structural parameters of 1,3,5-trinitro-1,3,5-triazacyclohexane (RDX), (CH2NNO2)3, 1,3-dinitro-1,3-diazacyclopentane (DDCP), CH2(CH2NNO2)2, and N-nitropyrrolidine (NP), (CH2)4NNO2, have been determined by electron diffraction. The six-membered ring of RDX has a chair form with axial positions of the nitro groups and close to planar bond geometry of the amine nitrogen atoms. The overall C3 symmetry of the molecule is in agreement with the experimental data. The conformation of the five-membered ring in DDCP is a half-chair of C2 symmetry, while that in NP is an envelope of CS symmetry. The nitro groups are in equatorial positions in both molecules. The conformations of pyrrolidine and imidazolidine cycles show interesting features. The pyramidal geometry of the amine nitrogen atom bonds flattens in going from pyrrolidine and N-chloropyrrolidine to NP and DDCP and then to RDX and to dimethylnitramine (DMNA), (CH3)2NNO2.",
author = "Shishkov, {Igor F.} and Vilkov, {Lev V.} and M. Kolonits and B{\'e}la Rozsondai",
year = "1991",
month = "1",
doi = "10.1007/BF00673490",
language = "English",
volume = "2",
pages = "57--64",
journal = "Structural Chemistry",
issn = "1040-0400",
publisher = "Springer New York",
number = "1",

}

TY - JOUR

T1 - The molecular geometries of some cyclic nitramines in the gas phase

AU - Shishkov, Igor F.

AU - Vilkov, Lev V.

AU - Kolonits, M.

AU - Rozsondai, Béla

PY - 1991/1

Y1 - 1991/1

N2 - The structural parameters of 1,3,5-trinitro-1,3,5-triazacyclohexane (RDX), (CH2NNO2)3, 1,3-dinitro-1,3-diazacyclopentane (DDCP), CH2(CH2NNO2)2, and N-nitropyrrolidine (NP), (CH2)4NNO2, have been determined by electron diffraction. The six-membered ring of RDX has a chair form with axial positions of the nitro groups and close to planar bond geometry of the amine nitrogen atoms. The overall C3 symmetry of the molecule is in agreement with the experimental data. The conformation of the five-membered ring in DDCP is a half-chair of C2 symmetry, while that in NP is an envelope of CS symmetry. The nitro groups are in equatorial positions in both molecules. The conformations of pyrrolidine and imidazolidine cycles show interesting features. The pyramidal geometry of the amine nitrogen atom bonds flattens in going from pyrrolidine and N-chloropyrrolidine to NP and DDCP and then to RDX and to dimethylnitramine (DMNA), (CH3)2NNO2.

AB - The structural parameters of 1,3,5-trinitro-1,3,5-triazacyclohexane (RDX), (CH2NNO2)3, 1,3-dinitro-1,3-diazacyclopentane (DDCP), CH2(CH2NNO2)2, and N-nitropyrrolidine (NP), (CH2)4NNO2, have been determined by electron diffraction. The six-membered ring of RDX has a chair form with axial positions of the nitro groups and close to planar bond geometry of the amine nitrogen atoms. The overall C3 symmetry of the molecule is in agreement with the experimental data. The conformation of the five-membered ring in DDCP is a half-chair of C2 symmetry, while that in NP is an envelope of CS symmetry. The nitro groups are in equatorial positions in both molecules. The conformations of pyrrolidine and imidazolidine cycles show interesting features. The pyramidal geometry of the amine nitrogen atom bonds flattens in going from pyrrolidine and N-chloropyrrolidine to NP and DDCP and then to RDX and to dimethylnitramine (DMNA), (CH3)2NNO2.

UR - http://www.scopus.com/inward/record.url?scp=0011266861&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0011266861&partnerID=8YFLogxK

U2 - 10.1007/BF00673490

DO - 10.1007/BF00673490

M3 - Article

AN - SCOPUS:0011266861

VL - 2

SP - 57

EP - 64

JO - Structural Chemistry

JF - Structural Chemistry

SN - 1040-0400

IS - 1

ER -