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Topological evidence for an NN bond in cis ‐1,2‐dinitrosoethene: The remarkable structure of the di‐ N ‐oxide of 1,2‐diazacyclobutadiene
Author(s) -
Sarasola C.,
Choi S. C.,
Ugalde J. M.,
Boyd Russell J.
Publication year - 1990
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.610030303
Subject(s) - chemistry , covalent bond , bond length , sextuple bond , bent bond , electron density , crystallography , atoms in molecules , oxide , molecule , bond order , single bond , molecular geometry , topology (electrical circuits) , computational chemistry , electron , crystal structure , physics , combinatorics , quantum mechanics , group (periodic table) , organic chemistry , mathematics
Analysis of the topological properties of the electron density distribution of cis ‐1,2‐dinitrosoethene (I) shows that there is a normal covalent, albeit very long, single bond between the nitrogen atoms in the molecule, which is in fact the di‐ N ‐oxide of 1,2‐diazacyclobutadiene (II). Despite its extraordinary length, the NN bond is shown to be consistent with the strong correlation between the electron density at the bond critical points and the calculated bond lengths of NN bonds. The geometry and electronic structure exhibit a number of remarkable features.