Nucleophile-Electrophile Interactions in 1,8-Disubstituted Naphthalenes: Structures of Three 1-Naphthaldehydes and a 1-Naphthyl Methyl Ketone

• Published in: Acta crystallographica. Section B, Structural science Vol. 54; no. 1; pp. 73 - 81
• Main Authors: Gallucci, J. C., Hart, D. J., Young, D. G. J.
• Format: Journal Article
• Language: English
• Published: 5 Abbey Square, Chester, Cheshire CH1 2HU, England International Union of Crystallography 01-02-1998; Blackwell
• Subjects: Aliphatic, non-condensed and condensed benzenic, and alicyclic compounds; Condensed matter: structure, mechanical and thermal properties; Exact sciences and technology; Organic compounds; Physics; Structure of solids and liquids; crystallography; Structure of specific crystalline solids; Molecular structure; Bicyclic compound; XRD; Interactions; Aldehydes; Ethers; Experimental study; Condensed benzenic compound; Organic compounds; Electrophile; Nucleophile; Crystal structure
• ISSN: 0108-7681; 1600-5740
• DOI: 10.1107/S0108768197009440

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.