Substituent effects in the benzene series: A structural approach

Domenicano, Aldo; Mazzeo, Pietro; Vaciago, A.

doi:10.1016/s0040-4039(00)77997-4

Cited by 124 publications

(74 citation statements)

References 12 publications

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“…In the benzene ring, the C-C bonds are regular with a mean value of 1.387 A. As reported previously (Domenicano, Vaciago & Coulson, 1975;Bavoux, Perrin, Thozet, Bertholon & Perrin, 1976), the internal angles of the benzene ring differ from 120 °, the values depending on the electronic prbperties of the substituents; the internal C (2)-C ( 1)-C (6) angle of 122.5 ° is greater than 120 ° , as has been found for about twenty phenols studied. In contrast, angles C(2)-C(3)-C(4) and C(1)-C(6)-C(5) are smaller than 120 °.…”

Section: Molecular Geometrysupporting

confidence: 82%

Structure of 2-isopropyl-5-methylphenol (thymol)

Thozet¹,

Perrin²

1980

Acta Crystallogr B Struct Crystallogr Cryst Chem

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The crystal structure of the title compound, C loHl4 O, has been determined from Cu Ka data by direct methods and refined to an R of 0.054. Crystals are trigonal, space group R3, with unit-cell parameters (hexagonal axes): a = b = 14.730 (2), c = 23.115 (3) A. There are 18 molecules in such a ceil. The molecular configuration shows the position of the isopropyl group relative to the benzene ring while the crystal structure shows hexamers of hydrogen-bonded molecules. The hexamers, centered at the vertices of rhombohedra, are linked by van der Waals contacts.

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Section: Molecular Geometrysupporting

confidence: 82%

Structure of 2-isopropyl-5-methylphenol (thymol)

Thozet¹,

Perrin²

1980

Acta Crystallogr B Struct Crystallogr Cryst Chem

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“…The internal angle ipso to the hydroxy group, aon = 120.5 (1) °, is slightly greater than the mean value of 120.2 ° derived from many structural results on para-substituted hydroxybenzenes (Domenicano, Mazzeo & Vaciago, 1976).…”

Section: The Benzene Ringcontrasting

confidence: 54%

Structural studies of benzene derivatives. VI. Refinement of the crystal structure of p-hydroxybenzoic acid monohydrate

Colapietro¹,

Domenicano²,

Marciante³

1979

Acta Crystallogr Sect B

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The crystal structure of p-hydroxybenzoic acid monohydrate, CTH6Oa.H20, determined from photographic data [Fukuyama, Ohkura, Kashino & Haisa (1973). Bull. Chem. Soc. Jpn, 46,[804][805][806][807][808], has been refined to R = 0.0414 on 1454 counter reflexions. Crystals are monoclinic, space group P2~/a, with a = 17.752 (9), b = 6.442 (2), c = 6.731 (3) A, fl= 105.48 (6)°, Z=4. The benzene ring has approximate C2, (mm) symmetry and shows a slight quinoidal shortening of the central C-C bonds. The internal angles at the ipso positions of the ring are aon = 120.5 (1) °, acoon = 119.4 (1) °.

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“…1 and Table 3(a)]. The relationship of such an angle in a benzene ring to the electronegativity of the substituent has been pointed out by Domenicano, Mazzeo & Vaciago (1975).…”

Section: Discussion Of Structnrementioning

confidence: 93%