Synthesis, Molecular and Crystal Structure Analysis of 1-(4-Methylbenzenesulfonyl)indole-3-carbaldehyde and DFT Investigation of Its Rotational Conformers

Author(s)

Zukerman-Schpector, Julio ^[1] ; Madureira, Lucas Sousa ^[1] ; Wulf, Glaudeston Dutra ^[1] ; Stefani, Helio A. ^[2] ; Vasconcelos, Stanley N. S. ^[2] ; Ng, Seik Weng ^{[3, 4]} ; Tiekink, Edward R. T. ^[3]

Affiliation

^[1] Univ Fed Sao Carlos, Dept Quim, Lab Cristal Estereodinam & Modelagem Mol, BR-13565905 Sao Carlos, SP - Brazil

^[2] Univ Sao Paulo, Fac Ciencias Farmaceut, Dept Farm, BR-05508900 Sao Paulo - Brazil

^[3] Univ Malaya, Dept Chem, Kuala Lumpur 50603 - Malaysia

^[4] King Abdulaziz Univ, Dept Chem, Fac Sci, Jeddah 80203 - Saudi Arabia

• Document type: Journal article
• Source: Molecules; v. 19, n. 2, p. 1990-2003, FEB 2014.
• Web of Science Citations: 0

Abstract

Two independent molecules that differ in terms of rotation about the central S-N bond comprise the asymmetric unit of the title compound 1. The molecules have a V-shape with the dihedral angles between the fused ring system and benzene ring being 79.08(6)degrees and 72.83(5)degrees, respectively. The packing is mostly driven by pi center dot center dot center dot pi interactions occurring between the tolyl ring of one molecule and the C-6 ring of the indole fused ring system of the other. DFT and IRC calculations for these and related 1-(arylsulfonyl)indole molecules showed that the rotational barrier about the S-N bond between conformers is within the 2.5-5.5 kcal/mol range. Crystal data for C16H13NO3S (1): Mr = 299.33, space group Pna2(1), a = 19.6152(4) angstrom, b = 11.2736(4) angstrom, c = 12.6334(3) angstrom, V = 2793.67(13) angstrom(3), Z = 8, Z' = 2, R = 0.034. (AU)

• FAPESP's process: 12/00424-2 - Synthesis of small libraries using potassium Organotrifluoroborates in Suzuki-Miyaura reactions
• Grantee: Helio Alexandre Stefani
• Support Opportunities: Research Projects - Thematic Grants