Conformational Mobility Study in Mono Quinone Derivative of Calix[4]arene by Low Temperature NMR Spectroscopy

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Author(s): Elham Hassibia, Saeed Taghvaei Ganjali*, Mohamad Mahmoodi Hashemi, Reza Zadmard, Shahram Moradi Dehaghi.

Journal Name: Letters in Organic Chemistry

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Abstract:

Calix[4]monoquinone (3) has been synthesized by oxidation of rigidly cone conformation of tripropoxy calix[4]arene (2), and conformational characteristics of this molecule has been studied by means of dynamic nuclear magnetic resonance (DNMR) and HH– correlated nuclear magnetic resonance spectroscopy (HH–COSY NMR). On the basis of the data that have been obtained free Gibbs energy of activation (ΔG#) for quinone ring interconversion process of 3 was determined 12.3±0.05 Kcal/mol by coalescence approximation method.

Keywords: Calix[4]arenes, Calixquinones, Coalescence Temperature, Conformational mobility, Pseudo flatted Cone conformation, flip flopping interconversion

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Article Details

(E-pub Ahead of Print)
DOI: 10.2174/1570178616666190228130119
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