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X‐Ray Diffraction Study of 2‐Aminopropenenitrile at 97 K
Author(s) -
Seiler Paul,
Dunitz Jack D.
Publication year - 1985
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19850680802
Subject(s) - chemistry , molecule , crystallography , nitrile , hydrogen bond , crystal structure , group (periodic table) , ab initio , acceptor , molecular orbital , crystal (programming language) , computational chemistry , organic chemistry , physics , condensed matter physics , computer science , programming language
2‐Aminopropenenitrile crystallizes in the space group P 2 1 2 1 2 1 with two molecules in the asymmetric unit. Both molecules show appreciable pyramidalization at the amino group. The crystal structure is built from approximately centrosymmetric dimers stabilized by hydrogen bonding between the amino group of each molecule and the nitrile group of its partner. The dimers are linked into chains by further hydrogen bonds in which the amino group of one molecule acts as donor, the amino group of the other as acceptor. The two types of molecule thus play different roles in the crystal structure. Electron density difference maps for the two independent molecules show characteristic bonding density features. The molecular structure as obtained by the low‐temperature X‐ray analysis is closely similar to that derived from ab initio molecular orbital calculations and leads to rotational constants close to those obtained from a microwave spectroscopic study.