Molecules 2014, 19(2), 1990-2003; doi:10.3390/molecules19021990
Article

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

1,* email, 1email, 1email, 2email, 2email, 3,4email and 3,* email
Received: 13 November 2013; in revised form: 25 January 2014 / Accepted: 28 January 2014 / Published: 13 February 2014
(This article belongs to the Section Organic Synthesis)
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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)° and 72.83(5)°, respectively. The packing is mostly driven by p···p interactions occurring between the tolyl ring of one molecule and the C6 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 Pna21, a = 19.6152(4) Å, b = 11.2736(4) Å, c = 12.6334(3) Å, V = 2793.67(13) Å3, Z = 8, Z' = 2, R = 0.034.
Keywords: indole-3-carbaldehyde; conformational isomerism; DFT; IRC; crystal structure analysis; X-ray diffraction
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MDPI and ACS Style

Zukerman-Schpector, J.; Madureira, L.S.; Wulf, G.D.; Stefani, H.A.; Vasconcelos, S.N.S.; Ng, S.W.; Tiekink, E.R.T. Synthesis, Molecular and Crystal Structure Analysis of 1-(4-Methylbenzenesulfonyl)indole-3-carbaldehyde and DFT Investigation of Its Rotational Conformers. Molecules 2014, 19, 1990-2003.

AMA Style

Zukerman-Schpector J, Madureira LS, Wulf GD, Stefani HA, Vasconcelos SNS, Ng SW, Tiekink ERT. Synthesis, Molecular and Crystal Structure Analysis of 1-(4-Methylbenzenesulfonyl)indole-3-carbaldehyde and DFT Investigation of Its Rotational Conformers. Molecules. 2014; 19(2):1990-2003.

Chicago/Turabian Style

Zukerman-Schpector, Julio; Madureira, Lucas S.; Wulf, Glaudeston D.; Stefani, Hélio A.; Vasconcelos, Stanley N.S.; Ng, Seik W.; Tiekink, Edward R.T. 2014. "Synthesis, Molecular and Crystal Structure Analysis of 1-(4-Methylbenzenesulfonyl)indole-3-carbaldehyde and DFT Investigation of Its Rotational Conformers." Molecules 19, no. 2: 1990-2003.

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