Barriers to internal rotation in 1, 3, 5-trineopentylbenzenes. VI. Correlation between barriers to internal rotation (. DELTA. G. dag.) and substituent size

B Nilsson, P Martinson, K Olsson…

Index: Nilsson,B. et al. Journal of the American Chemical Society, 1974 , vol. 96, p. 3190 - 3197

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Citation Number: 31

Abstract

Abstract: Relative “effective sizes” of the substituents H, F, C1, Br, CH3, and I in the 1, 3, 5- trineopentylbenzene system have been estimated from AG* values obtained by dynamic nmr measurements of rotational barriers, ranging from 5.4 to 18.8 kcal/mol. An increase in barrier height with increasing substituent van der Waals volume was observed. The methyl group was found to be between chlorine and bromine in size in the trineopentylbenzene ...