Crystal Structure of 1,2-Diphenyl-3-nitrocyclopropene and ab Initio Calculations of 3-Nitrocyclopropene

Document Type

Article

Publication Date

1-1-1988

Abstract

The structural ambiguity regarding the identity of the reaction product of 1, 2-diphenylcyclopropenium perchlorate and sodium nitrite in acetic anhydride has been resolved in favor of the 3-nitrocyclopropene alternative. The molecule in the solid state adopts the bisected conformation, compatible with the theoretically calculated structure and characteristic of other π-acceptors attached to three-membered carbocyclic rings. The ring dimensions and especially the very long C-N bond indicate a tendency toward unprecedented facile heterolysis of the C-NO2 bond to form nitrite anion and a cation; this tendency is only slightly apparent in the isolated (model) 3-nitrocyclopropene. © 1988, American Chemical Society. All rights reserved.

Identifier

0000778154 (Scopus)

Publication Title

Journal of the American Chemical Society

External Full Text Location

https://doi.org/10.1021/ja00209a037

e-ISSN

15205126

ISSN

00027863

First Page

226

Last Page

230

Issue

1

Volume

110

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