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- Title
Structural Studies of 1,8-Disubstituted Naphthalenes as Probes for nucleophile-electrophile interactions.
- Authors
Schweizer, W. Bernd; Procter, Garry; Kaftory, Menahem; Dunitz, Jack D.
- Abstract
Results of crystal structure analyses of seven 1, 8-disubstituted naphthalenes ( 2a, 8-( N,N-dimethylamino)-1-naphthyl methyl ketone; 2b, 8-( N, N-dimethylamino)naphthalene-1-carboxylic acid; 2c, methyl 8-( N, N-dimethylamino)naphthalene-1-carboxylate; 2d, 8-methoxy-1-naphthyl methyl ketone; 2e, 8-methoxynaphthalene-1-carboxylic acid; 2f, N, N-dimethyl-8-methoxynaphthalene 1-carboxamide; 2g, N, N-dimethyl-8-hydroxynaphthalene-1-carboxamide) with a nucleophilic centre (N(CH3)2, OCH3, OH) at one of the peri positions and an electrophilic centre (carbonyl C) at the other are described. All seven molecules show a characteristic distortion pattern: the exocyclic bond to the electrophilic centre is splayed outward, and the one to the nucleophilic centre is splayed inward; the carbonyl C is displaced from the plane of its three bonded atoms towards the nucleophile. This distortion pattern differs from that found in other 1,8-disubstituted naphthalenes and is interpreted as an expression of incipient nucleophilic addition to a carbonyl group. The crystal structure of 2b contains an ordered arrangement of equal numbers of amino acid and zwitterionic molecules.
- Publication
Helvetica Chimica Acta, 1978, Vol 61, Issue 8, p2783
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19780610806