Iso­propyl 2,4,6-triiso­propyl­phenyl sulfone: an aryl sulfone with unusual atom deviations from the aromatic least-squares plane

P B Sandrock; C Y Meyers; Nigam Rath; P. D. Robinson

doi:10.1107/S1600536804004635

Isopropyl 2,4,6-triisopropylphenyl sulfone: an aryl sulfone with unusual atom deviations from the aromatic least-squares plane

P B Sandrock, C Y Meyers, Nigam Rath, P. D. Robinson

University of Missouri-St. Louis

Research output: Contribution to journal › Article › peer-review

Abstract

<div class="line" id="line-11"> Isopropyl 2,4,6-triisopropylphenyl sulfone, C 18 H 30 O 2 S, (I), has been synthesized for the first time. In spite of the bulky isopropyl substituents on both  ortho  positions, crystalline (I) does not exhibit rotational disorder of the isopropyl group bonded to the sulfonyl. In contrast, the corresponding bromo- and chloroisopropyl groups of crystalline aryl sulfones possessing much smaller di- ortho -methyl substituents display striking rotational disorder. While the aryl rings of the latter compounds are essentially planar, considerable atom deviation from the aromatic least-squares plane of (I) was observed. None of the intra- or intermolecular distances between the methyl C atoms of the sulfonylisopropyl group and those of the two  ortho -isopropyl groups of (I) is shorter than the sum of their van der Waals radii, making it unlikely that they would interfere with the rotation of the  <img src="http://scripts.iucr.org/logos/entities/alpha_rmgif.gif"/> -isopropyl group prior to crystallization. </div>

Original language	American English
Journal	Acta Crystallographica
Volume	60
DOIs	https://doi.org/10.1107/S1600536804004635
State	Published - 2004

Disciplines

Life Sciences
Biochemistry, Biophysics, and Structural Biology
Biochemistry

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10.1107/S1600536804004635License: Unspecified

Cite this

@article{9ab56cd50b9f483ea8a0327c9a9c4939,

title = "Isopropyl 2,4,6-triisopropylphenyl sulfone: an aryl sulfone with unusual atom deviations from the aromatic least-squares plane",

abstract = " Isopropyl 2,4,6-triisopropylphenyl sulfone, C 18 H 30 O 2 S, (I), has been synthesized for the first time. In spite of the bulky isopropyl substituents on both  ortho  positions, crystalline (I) does not exhibit rotational disorder of the isopropyl group bonded to the sulfonyl. In contrast, the corresponding bromo- and chloroisopropyl groups of crystalline aryl sulfones possessing much smaller di- ortho -methyl substituents display striking rotational disorder. While the aryl rings of the latter compounds are essentially planar, considerable atom deviation from the aromatic least-squares plane of (I) was observed. None of the intra- or intermolecular distances between the methyl C atoms of the sulfonylisopropyl group and those of the two  ortho -isopropyl groups of (I) is shorter than the sum of their van der Waals radii, making it unlikely that they would interfere with the rotation of the  -isopropyl group prior to crystallization. ",

author = "Sandrock, {P B} and Meyers, {C Y} and Nigam Rath and Robinson, {P. D.}",

note = "Isopropyl 2,4,6-triisopropylphenyl sulfone, CHOS, (I), has been synthesized for the first time. In spite of the bulky isopropyl substituents on both ortho positions, crystalline (I) does not exhibit rotational disorder of the isopropyl group bonded to the sulfonyl. In contrast, the corresponding bromo- and chloroisopropyl groups of crystalline aryl sulfones possessing much smaller di- ortho-methyl substituents display striking rotational disorder.",

year = "2004",

doi = "10.1107/S1600536804004635",

language = "American English",

volume = "60",

journal = "Acta Crystallographica",

}

TY - JOUR

T1 - Isopropyl 2,4,6-triisopropylphenyl sulfone: an aryl sulfone with unusual atom deviations from the aromatic least-squares plane

AU - Sandrock, P B

AU - Meyers, C Y

AU - Rath, Nigam

AU - Robinson, P. D.

N1 - Isopropyl 2,4,6-triisopropylphenyl sulfone, CHOS, (I), has been synthesized for the first time. In spite of the bulky isopropyl substituents on both ortho positions, crystalline (I) does not exhibit rotational disorder of the isopropyl group bonded to the sulfonyl. In contrast, the corresponding bromo- and chloroisopropyl groups of crystalline aryl sulfones possessing much smaller di- ortho-methyl substituents display striking rotational disorder.

PY - 2004

Y1 - 2004

N2 - Isopropyl 2,4,6-triisopropylphenyl sulfone, C 18 H 30 O 2 S, (I), has been synthesized for the first time. In spite of the bulky isopropyl substituents on both  ortho  positions, crystalline (I) does not exhibit rotational disorder of the isopropyl group bonded to the sulfonyl. In contrast, the corresponding bromo- and chloroisopropyl groups of crystalline aryl sulfones possessing much smaller di- ortho -methyl substituents display striking rotational disorder. While the aryl rings of the latter compounds are essentially planar, considerable atom deviation from the aromatic least-squares plane of (I) was observed. None of the intra- or intermolecular distances between the methyl C atoms of the sulfonylisopropyl group and those of the two  ortho -isopropyl groups of (I) is shorter than the sum of their van der Waals radii, making it unlikely that they would interfere with the rotation of the  -isopropyl group prior to crystallization.

AB - Isopropyl 2,4,6-triisopropylphenyl sulfone, C 18 H 30 O 2 S, (I), has been synthesized for the first time. In spite of the bulky isopropyl substituents on both  ortho  positions, crystalline (I) does not exhibit rotational disorder of the isopropyl group bonded to the sulfonyl. In contrast, the corresponding bromo- and chloroisopropyl groups of crystalline aryl sulfones possessing much smaller di- ortho -methyl substituents display striking rotational disorder. While the aryl rings of the latter compounds are essentially planar, considerable atom deviation from the aromatic least-squares plane of (I) was observed. None of the intra- or intermolecular distances between the methyl C atoms of the sulfonylisopropyl group and those of the two  ortho -isopropyl groups of (I) is shorter than the sum of their van der Waals radii, making it unlikely that they would interfere with the rotation of the  -isopropyl group prior to crystallization.

UR - https://doi.org/10.1107/S1600536804004635

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M3 - Article

VL - 60

JO - Acta Crystallographica

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