Conformational study of a strained tolanophane by dynamic 1H NMR spectroscopy and computational methods |
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Authors: | Hossein Reza Darabi Marjan Azimzadeh Arani Mohsen Tafazzoli Mina Ghiasi |
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Affiliation: | (1) Chemistry and Chemical Engineering Research Center of Iran, Tehran, Iran;(2) Chemistry Department, Sharif University of Technology, Tehran, Iran |
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Abstract: | The existence of a short C–H ⋯ π (alkyl–alkyne) interaction in the structure of a strained and relatively rigid tolanophane is expected to hinder the rotation about the C–C sp3 single bond. Variable-temperature NMR experiments (performed in three solvents, CDCl3, THF-d8, and acetone-d6) and ab initio density functional calculations were carried out to investigate its dynamic nature. An energy barrier of 48.6 kJ/mol is determined at coalescence (210 K) with acetone-d6 which is in good agreement with calculation result (54 kJ/mol). Correspondence: Hossein Reza Darabi, Chemistry and Chemical Engineering Research Center of Iran, Pajoohesh Blvd., km 17, Karaj Hwy, 14968-13151 Tehran, Iran. |
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Keywords: | Tolanophane Strain Dynamic 1H NMR Ab initio calculations. |
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