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Calculated structures and relative stabilities of furoxan, some 1,2‐dinitrosoethylenes and other isomers
Author(s) -
Seminario Jorge M.,
Concha Monica C.,
Politzer Peter
Publication year - 1992
Publication title -
journal of computational chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.907
H-Index - 188
eISSN - 1096-987X
pISSN - 0192-8651
DOI - 10.1002/jcc.540130209
Subject(s) - furoxan , computational chemistry , chemistry , mathematics , organic chemistry , nitric oxide
The structures and relative stabilities of furoxan and some of its isomers, e.g., the 1,2‐dinitrosoethylenes, have been determined by means of ab initio Hartee–Fock and Møller–Plesset calculations. Geometries were optimized at the HF/3‐21G, HF/6‐31G* and MP2/6‐31G* levels, and subsequently used for computing MP2/6‐31G*, MP3/6‐31G*, and MP4/6‐31G* energies. The results are markedly affected by the inclusion of electronic correlation, which renders three of the isomers unstable. It also emphasizes the importance of a zwitterionic contribution to the structure of furoxan, which promotes ring‐opening through a cis 1,2‐dinitrosoethylene intermediate/transition state that has an MP4/6‐31G*//MP2/6‐31G* energy that is 31.6 kcal/mol above furoxan.