The crystal structure of tetramethyl-<i>p</i>-phenylene ditoluene-<i>p</i>-sulphonate

Wieczorek, M. W.; Bokiy, N. G.; Struchkov, Yu. T.

doi:10.1107/s056774087500828x

Cited by 6 publications

(3 citation statements)

References 6 publications

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“…The crystal structure of the title compound was determined because of the biological importance of its analogues. A search of Version 5.23 (July 2002 updates) of the Cambridge Structural Database (Allen, 2002) revealed 16 structures [refcodes KAWDAN (Niestroj et al, 1998), FIXCAQ (Chinnakali et al, 1999), NEDXUP, NEDYAW and NEDYIE (Gallucci et al, 1998), NUNCII (Goswami et al, 1998), RASSOT (Işik et al, 1997), RELVUZ (Bott et al, 1996), SIMVUF (Bindal et al, 1990), TCPTOS (Wieczorek & Galdecki, 1978), TEBFOV (Prince et al, 1991), TMPDTS (Wieczorek et al, 1975), TSMIPH (Sarkar & Gupta, 1980), WOHCUR (Meents et al, 2000), ZZZBDA10 (Wieczorek, 1980) and MIWHIJ (Lee et al, 2001)] that are closely related to the title compound in having benzene rings attached to the sulfonate group. The S-C, S-O and S O bond lengths (Table 1) are comparable to those found in related structures (Vembu, Nallu, Garrison & Youngs, 2003a,b,c,d,e,f;Vembu, Nallu, Spencer & Howard, 2003a,b,c,d,e,f,g;Vembu et al, 2003;Vembu, Nallu, Durmus et al, 2004a,b,c).…”

Section: Commentmentioning

confidence: 99%

Phenyl 4-toluenesulfonate: supramolecular aggregation through weak C—H...O and C—H...π interactions

et al. 2005

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Section: Commentmentioning

confidence: 99%

Phenyl 4-toluenesulfonate: supramolecular aggregation through weak C—H...O and C—H...π interactions

et al. 2005

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“…An X-ray crystallographic study of the title compound, (I), was undertaken in order to determine its structure, owing to the biological importance of its analogues. A search of version 5.23 (July 2002 updates) of the Cambridge Structural Database (Allen, 2002) revealed 16 structures [refcodes KAWDAN (Niestroj et al, 1998), FIXCAQ (Chinnakali et al, 1999), NEDXUP, NEDYAW, NEDYIE (Gallucci et al, 1998), NUNCII (Goswami et al, 1998), RASSOT (Işik et al, 1997), RELVUZ (Bott et al, 1996), SIMVUF (Bindal et al, 1990), TCPTOS (Wieczorek & Galdecki, 1978), TEBFOV (Prince et al, 1991), TMPDTS (Wieczorek et al, 1975), TSMIPH (Sarkar & Gupta, 1980), WOHCUR (Meents et al, 2000), ZZZBDA10 (Wieczorek, 1980) and MIWHIJ (Lee et al, 2001)] that are closely related to the title compound in having benzene rings attached to the sulfonate group. The S-C, S-O and S O bond lengths (Table 1) are comparable to those found in related structures (Vembu et al, 2004, and references therein;Manivannan et al, 2005, and references therein).…”

Section: Commentmentioning

confidence: 99%

4-Bromophenyl 4-toluenesulfonate: supramolecular aggregation through weak C—H...O and C—H...π interactions

et al. 2005

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In the crystal structure of the title compound, C13H11BrO3S, the dihedral angle between the mean planes of the 4‐tolyl and 4‐bromophenyl rings is 67.3 (2)°. There are weak C—H⋯O hydrogen bonds which generate rings of graph‐set motifs S(5), S(6), R12(4), R21(6) and R22(8). The supramolecular aggregation is completed by the presence of C—H⋯π interactions. An R22(7) motif formed by the combination of a C—H⋯O and a C—H⋯π interaction is a notable feature in the title compound.

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“…Two of these compounds are closely related to compound 2. The first, 5-bromo-2,3-dimethylphenol-1-(4-methylphenylsulfonyloxy)benzene (KAWDAN;Niestroj et al, 1998), is built up from a tosylate attached to a phenyl ring substituted by two methyl groups and one bromine atom whereas the second, tetramethyl-pphenylene p-ditoluenesulfonate (TMPDTS; Wieczorek et al, 1975), is built up from a tetramethyl-substituted phenyl ring attached to two tosylate units. A comparison of selected distances in compound 2 with those of two structures reveals that the geometries are very similar for all three compounds ( Table 2).…”

Section: Database Surveymentioning

confidence: 99%

Crystal structure of 2-isopropyl-4-methoxy-5-methylphenyl 4-methylbenzenesulfonate

Laamari¹,

Auhmani²,

Itto³

et al. 2018

Acta Cryst E

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The title compound, C 18 H 22 O 4 S, an hemisynthetic product, was obtained by the tosylation reaction of the naturally occurring meroterpene p-methoxythymol. The molecule comprises a tetrasubstitued phenyl ring linked to a toluenesulfonate through one of its O atoms. In the crystal, C-HÁ Á ÁO and C-HÁ Á Á interactions link the molecules, forming a three-dimensional network. Chemical contextTosylation of alcohols is an important transformation in organic synthesis. This transformation is usually achieved with p-toluene sulfonyl chloride, which is very reactive (Greene & Wuts, 1999;Yoshida et al., 1999). Tosylate is an important functional group in organic synthesis as it makes a good leaving group (Wagner & Zokk, 1955;Sandler & Karo, 1983). Indeed, tosylates are used as intermediates in the synthesis of several drugs (Kim et al., 1995;Morgan et al., 1997). Furthermore, they have also been found to possess important biological activities (Kacem et al., 2002;Kaleemullah et al., 2012).The hemisynthesis of 2-isopropyl-4-methoxy-5-methylphenyl 4-methylbenzenesulfonate 2 from naturally occurring p-methoxythymol 1 was undertaken with the aim of preparing meroterpenic tosylate. X-ray single-crystal structure analysis allowed its full structure to be confirmed unambiguously. Structural commentaryCompound 2 is built up from a tetrasubstituted phenyl ring linked to a toluenesulfonate unit through one of its oxygen atoms (Fig. 1). The two phenyl rings form a dihedral angle of 60.03 (9) . Atoms S1 and C5 0 are coplanar with the C1 0 -C6 0 phenyl ring, their distances from the plane being 0.057 (3) and 0.031 (3) Å , respectively. Considering the connected atoms of ISSN 2056-9890 the four substituents on the C1-C6 phenyl ring, three of them O2, C8 and C11 are roughly in the plane of the phenyl ring, deviating by only 0.011 (3), 0.014 (3) and 0.012 (3) Å , respectively, from the mean plane, whereas atom O1 is displaced slightly out of the plane by 0.101 (3) Å . This slight distortion might be related to the occurrence of a weak C-HÁ Á Á interaction between the C9 atom and the centroid Cg2 of the C1 0 -C6 0 phenyl ring (Table 1). Supramolecular featuresIn the crystal, pairs of molecules are linked though C-HÁ Á ÁO interactions (Table 1), forming pseudo-dimer arranged around inversion centers (Fig. 2). Further C-HÁ Á ÁO hydrogen bonds and C-HÁ Á Á interactions (Table 1, Fig. 2) lead to the formation of a three-dimensional network. Database surveyA search of the Cambridge Structural Database (CSD, version 5.38, last update May 2017; Groom et al., 2016) for a tosylate fragment bearing an organic substituent on one of its oxygen atoms revealed only three hits. Two of these compounds are closely related to compound 2. The first, 5-bromo-2,3-dimethylphenol-1-(4-methylphenylsulfonyloxy)benzene (KAWDAN; Niestroj et al., 1998), is built up from a tosylate attached to a phenyl ring substituted by two methyl groups and one bromine atom whereas the second, tetramethyl-pphenylene p-ditoluenesulfonate (TMPDTS; Wieczorek et al., 1975), is b...

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The crystal structure of tetramethyl-p-phenylene ditoluene-p-sulphonate

Cited by 6 publications

References 6 publications

Phenyl 4-toluenesulfonate: supramolecular aggregation through weak C—H...O and C—H...π interactions

Phenyl 4-toluenesulfonate: supramolecular aggregation through weak C—H...O and C—H...π interactions

4-Bromophenyl 4-toluenesulfonate: supramolecular aggregation through weak C—H...O and C—H...π interactions

Crystal structure of 2-isopropyl-4-methoxy-5-methylphenyl 4-methylbenzenesulfonate

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