strain enthalpy
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2016 ◽  
Vol 9 (1) ◽  
pp. 6-13 ◽  
Author(s):  
Martin Michalík ◽  
Peter Poliak ◽  
Vladimír Lukeš

Abstract The substituent effect on the geometry and strain enthalpy of [2,2]paracyclophane is theoretically investigated by density functional theory. Gas-phase calculations were performed for twenty distinct electron donating and electron withdrawing substituents. The largest out-of-plane distortion of phenyl rings is exhibited by —SCN and —CF3 groups. On the other hand, —OH, —CH3 and —F groups show the minimal deformation. The strain enthalpy for unsubstituted [2,2]paracyclophane associated with repulsive forces between phenyl units reached up to 118.5 kJ mol−1. Any substitution causes increase of the strain enthalpy value proportionally to the absolute values of Hammett para-substituent constants. Two separate linear dependences with similar slopes were obtained for monosubstituted as well as double symmetrically substituted derivatives.


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