Issue 11, 2000

The solid- and solution-state structures of 2-nitrosopyridine and its 3- and 4-methyl derivatives

Abstract

2-Nitrosopyridine, 1, 3-methyl-2-nitrosopyridine, 2, and 4-methyl-2-nitrosopyridine, 3, exist in organic solvents as monomer–azodioxy dimer equilibria with the dimers predominating at ambient temperatures. In the case of compounds 1 and 3 only the Z-dimers co-exist with the monomers, whereas for compound 2 both Z- (major) and E- (minor) dimers are present with the monomer. Variable temperature 1H NMR bandshape analysis and 2D-EXSY spectra of 1–3 provided thermodynamic and kinetic data for the dissociation equilibria Z- (or E-) dimer ⇌ 2 monomer, ΔH [circle, cut, short horiz bar] values being in the range 53–58 kJ mol−1 and ΔG (298.15 K) values in the range 70–82 kJ mol−1. An X-ray crystal structure of 1 identified the compound as a Z-dimeric species with the two pyridine rings twisted by 62.7° and their heterocyclic N atoms pointing towards each other.

Supplementary files

Article information

Article type
Paper
Submitted
30 May 2000
Accepted
05 Sep 2000
First published
19 Oct 2000

J. Chem. Soc., Perkin Trans. 2, 2000, 2280-2286

The solid- and solution-state structures of 2-nitrosopyridine and its 3- and 4-methyl derivatives

B. G. Gowenlock, M. J. Maidment, K. G. Orrell, V. Šik, G. Mele, G. Vasapollo, M. B. Hursthouse and K. M. Abdul Malik, J. Chem. Soc., Perkin Trans. 2, 2000, 2280 DOI: 10.1039/B004270F

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