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4,8-Dimethoxy-5-(tosyloxy)-1-naphthaldehyde (1) and 8-methoxy-5-(tosyloxy)-1-naphthaldehyde (2) crystallize such that the formyl groups approach coplanarity with the naphthalene rings. 4′,8′-Dimethoxy-5′-(tosyloxy)-1′-acetonaphthone (4), however, crystallizes such that the acetyl group approaches orthogonality to the naphthalene ring. In all three compounds the methoxy group and carbonyl groups exhibit a leaning effect typical of nucleophile–electrophile interactions in 1,8-disubstituted naphthalenes. 8-(Benzoyloxy)-4-methoxy-1-naphthaldehyde (3) crystallizes with the formyl group nearly coplanar to the naphthalene ring and does not exhibit the leaning effect. It is suggested that these structural differences are largely due to differences in the steric requirements of formyl and acetyl groups.

Supporting information

cif

Crystallographic Information File (CIF)
Contains datablocks global, Hart1, Hart2, Hart3, Hart4

CCDC references: 131703; 131704; 131705; 131706

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