2,4-Bis[1-(4-hydroxyphenyl)-1-methylethyl]phenol: a three-dimensional framework built from O-H...O hydrogen bonds

Ewa Rozycka-Sokolowska1

  • 1Institute of Chemistry and Environmental Protection, Jan Dlugosz University, Armii Krajowej 13/15, 42-200 Czestochowa, Poland. crystal@cz.onet.pl

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Overview
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Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
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Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
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