Structure of 4,4-Bisphenylsulfonyl-N,N-dimethylbutylamine: Interplay of Intramolecular C–H···N, C–H···O=S, and π···π Interactions

Jiong Ran; Ming Wah Wong

doi:10.1071/CH09303

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Structure of 4,4-Bisphenylsulfonyl-N,N-dimethylbutylamine: Interplay of Intramolecular C–H···N, C–H···O=S, and π···π Interactions

Jiong Ran ^A and Ming Wah Wong ^A ^B

+ Author Affiliations

- Author Affiliations

^A Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore.

^B Corresponding author. Email: chmwmw@nus.edu.sg

Australian Journal of Chemistry 62(9) 1062-1067 https://doi.org/10.1071/CH09303
Submitted: 20 May 2009 Accepted: 23 July 2009 Published: 17 September 2009

Abstract

Conformations of 4,4-bisphenylsulfonyl-N,N-dimethylbutylamine (BSDBA) were examined by ab initio calculations. Intramolecular C–H···N, C–H···O, and π···π interactions are found to play an important role in governing the conformational properties. This finding is supported by charge density analysis based on the theory of atoms in molecules. The calculated molecular structure and ¹H chemical shifts of the methyl derivative (BSTBA) are in excellent agreement with experimental findings. The intramolecular C–H···N hydrogen bond in BSDBA is estimated to have a significant interaction energy of 25 kJ mol^–1. The sulfonyl oxygens in BSDBA interact readily with neighbouring methylene, methyl and phenyl hydrogens via C–H···O=S hydrogen bonds. In agreement with experiment, solvent effect calculations indicate that these weaker intramolecular interactions prevail in an aprotic polar medium.

Acknowledgements

This work was supported by the National University of Singapore.

References

Structure of 4,4-Bisphenylsulfonyl-N,N-dimethylbutylamine: Interplay of Intramolecular C–H···N, C–H···O=S, and π···π Interactions

Abstract

Acknowledgements

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