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

Gowenlock, B. G., Maidment, M. J., Orrell, K. G., Sik, V., Mele, G., Vasapollo, G., Hursthouse, M. B. and Malik, K. M. A. (2000) The solid- and solution-state structures of 2-nitrosopyridine and its 3-and 4-methyl derivatives Journal of the Chemical Society, Perkin Transactions 2, (11), pp. 2280-2286. (doi:10.1039/b004270f).

Record type: Article


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 H-1 NMR bandshape analysis and 2D-EXSY spectra of 1-3 provided thermodynamic and kinetic data for the dissociation equilibria Z- (or E-) dimer reversible arrow 2 monomer, DeltaH(empty set) values being in the range 53-58 kJ mol(-1) and DeltaG double dagger (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 degrees and their heterocyclic N atoms pointing towards each other.

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Published date: 2000
Keywords: crystal-structures, c-nitrosobenzenes, nitroso group, nitrosopyrazoles, trans, cis


Local EPrints ID: 18913
ISSN: 1364-5471
PURE UUID: a8f3bcc5-c733-48ce-a1cd-a8d91cec8f65

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Date deposited: 21 Dec 2005
Last modified: 17 Jul 2017 16:34

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Author: B. G. Gowenlock
Author: M. J. Maidment
Author: K. G. Orrell
Author: V. Sik
Author: G. Mele
Author: G. Vasapollo
Author: M. B. Hursthouse
Author: K. M. A. Malik

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