Abstract

A series of 13 enantiopure aryl benzyl sulfoxides (1a, 1b, 1c, 1d, 1e, 1f, 1g, 1h, 1i, 1j, 1k, 1l, 1m) with different substituents on the two aromatic rings has been previously analyzed by means of electronic circular dichroism (CD) spectroscopy. Most of these compounds are crystalline and their X-ray structure is established. For almost one-half of the series, CD spectra measured in the solid state were quite different from those in acetonitrile solution. We demonstrate that the difference is due to strong exciton couplings between molecules packed closely together in the crystal. The computational approach consists of time-dependent density functional theory (TDDFT) calculations run on "dimers" composed of nearest neighbors found in the lattice. Solid-state CD spectra are well reproduced by the average of all possible pairwise terms. The relation between the crystal space group and conformation, and the appearance of solid-state CD spectra, is also discussed. Chirality 26:102-110, 2013. © 2013 Wiley Periodicals, Inc. © 2013 Wiley Periodicals, Inc.

Autore Pugliese

• Cardellicchio Cosimo

Tutti gli autori

• Padula D.; Di Pietro S.; Capozzi; M.A.M.; Cardellicchio C.; Pescitelli G.

Titolo volume/Rivista

Chirality

Anno di pubblicazione

2014

ISSN

1520-636X

ISBN

Non Disponibile

Numero di citazioni Wos

Nessuna citazione

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Numero di citazioni Scopus

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Ultimo Aggiornamento Citazioni

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Settori ERC

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Codici ASJC

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