Crystal Structure of the Explosive Parent Benzyne Precursor: 2-Diazoniobenzenecarboxylate Hydrate

Author

Christopher J. Horan
Charles Leslie Barnes
Rainer Glaser, Missouri University of Science and TechnologyFollow

Abstract

The structure of the highly unstable benzyne precursor 2-diazoniobenzenecarboxylate (3) has been determined by single-crystal X-ray diffraction. The structure is discussed in comparison to ab initio results for several conformers of 3, related aromatic diazonium ions, and phenyl cation and also to crystal structures of simple diazonium ion salts and of benzoates. Structural features and characteristic distortions are related to the electron density distributions and to intra- and intermolecular interactions between the neighboring functional groups.

Recommended Citation

C. J. Horan et al., "Crystal Structure of the Explosive Parent Benzyne Precursor: 2-Diazoniobenzenecarboxylate Hydrate," Chemische Berichte, vol. 126, no. 1, pp. 243 - 249, Wiley-Blackwell, Jan 1993.

The definitive version is available at https://doi.org/10.1002/cber.19931260133

Department(s)

Chemistry

Keywords and Phrases

2-Diazoniobenzenecarboxylate; Benzyne Precursor; Calculations; Ab Initio; MO; Incipient Nucleophilic Attack; Neighboring Group Interactions

International Standard Serial Number (ISSN)

0009-2940

Document Type

Article - Journal

Document Version

Citation

File Type

text

Language(s)

English

Rights

© 1993 Wiley-Blackwell, All rights reserved.

Publication Date

01 Jan 1993