Allyl 4-hydroxybenzoate

Herrera, Ana M.; Bernès, Syl­vain; López, Delia

doi:10.1107/s1600536803019962

Cited by 3 publications

(6 citation statements)

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“…Regardless of the position for the CH 2 fragment, O-allyl chain displays the expected anticlinal conformation, characterized by torsion angles O-CH 2 -CH═CH 2 of -111 (2)° and 119.1 (4)°. A similar disorder was previously observed for a closely related phenol allylic derivative, allyl-4-hydroxybenzoate (Herrera et al, 2003). To date, only two acyclic allyl carbonate systems have been X ray characterized, both with non disordered allyl groups.…”

Section: S1 Commentsupporting

confidence: 75%

“…The crystal structures of two allyl carbonates have been reported to date, see: Michelet et al (2003); Burns & Forsyth (2008). For the use of allyl ester and allyl carbonate derivatives as precursors for organic glasses, see: Herrera et al (2003); Herrera (2006).…”

Section: Related Literaturementioning

confidence: 99%

“…We have synthesized some functionalized aromatic allyl ester (Herrera et al, 2003) and allyl carbonate compounds (Herrera, 2006) as intermediates in the preparation of new diallylcarbonate monomers, which are potential precursors of organic glasses. One representative example is the title molecule, which includes phenol and allyl functional groups as substitutents of the carbonate core (Fig.…”

Section: S1 Commentmentioning

confidence: 99%

“…This very limited set of structurally characterized allyl carbonate derivatives does not allow to determine the factors influencing the stable conformation for these molecules in the solid state. In contrast, a number of allyl ester derivatives have been X-ray characterized, with conformations restricted to two attractors (Herrera et al, 2003).…”

Section: S1 Commentmentioning

confidence: 99%

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Allyl 4-hydroxyphenyl carbonate

2009

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The title molecule, C10H10O4, is a functionalized carbonate used in the synthetic route to organic glasses. The central CH fragment of the allyl group is disordered over two positions, with occupancies in a 0.758 (10):0.242 (10)ratio. This disorder reflects the torsional flexibility of the oxygen–allyl group, although both disordered parts present the expected anticlinal conformation, with O—CH2—CH=CH2 torsion angles of −111 (2) and 119.1 (4)°. The crystal structure is based on chains parallel to [010], formed by O⋯H—O hydrogen bonds involving hydroxyl and carbonyl groups as donors and acceptors, respectively. The molecular packing is further stabilized by two weak C—H⋯π contacts from the benzene ring of the asymmetric unit with two benzene rings of neighboring molecules.

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Section: S1 Commentsupporting

confidence: 75%

Section: Related Literaturementioning

confidence: 99%

Section: S1 Commentmentioning

confidence: 99%

Section: S1 Commentmentioning

confidence: 99%

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Allyl 4-hydroxyphenyl carbonate

2009

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“…The molecule has an extended, slightly bow-shaped conformation, the dihedral angle between the two benzene ring being 76.02 (7) . The bond distances involving O atoms (Table 1) are in agreement with those found in related compounds (Chen et al, 2006;Herrera et al, 2003).…”

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confidence: 85%

Diethyl 4,4′-(butane-1,4-diyldioxy)dibenzoate

Li-mei

Kan

2007

Acta Crystallogr E Struct Rep Online

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Four Polymorphs of Methyl Paraben: Structural Relationships and Relative Energy Differences

Gelbrich

Braun

Ellern

et al. 2013

Crystal Growth & Design

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Four polymorphic forms of methyl paraben (methyl 4-hydroxybenzoate, 1), denoted 1-I (melting point 126 °C), 1-III (109 °C), 1-107 (107 °C), and 1-112 (112 °C), have been investigated by thermomicroscopy, infrared spectroscopy, and X-ray crystallography. The crystal structures of the metastable forms 1-III, 1-107, and 1-112 have been determined. All polymorphs contain the same O–H···O=C connected catemer motif, but the geometry of the resulting H-bonded chain is different in each form. The Z′ = 3 structure of 1-I (stable form; space group Cc) contains local symmetry elements. The crystal packing of each of the four known crystal structures of 1 was compared with the crystal structures of 12 chemical analogues. Close two-dimensional relationships exist between 1-112 and a form of methyl 4-aminobenzoate and between 1-107 and dimethyl terephthalate. The lattice energies of the four methyl paraben structures have been calculated with a range of methods based on ab initio electronic calculations on either the crystal or single molecule. This shows that the differences in the induction energy of the different hydrogen-bonded chain geometries have a significant effect on relative lattice energies, but that conformational energy, repulsion, dispersion, and electrostatic also contribute.

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Allyl 4-hydroxybenzoate

Abstract: Key indicatorsSingle-crystal X-ray study T = 296 K Mean '(C±C) = 0.003 A Ê Disorder in main residue R factor = 0.052 wR factor = 0.151 Data-to-parameter ratio = 12.7For details of how these key indicators were automatically derived from the article, see

Cited by 3 publications

References 4 publications

Allyl 4-hydroxyphenyl carbonate

Allyl 4-hydroxyphenyl carbonate

Diethyl 4,4′-(butane-1,4-diyldioxy)dibenzoate

Four Polymorphs of Methyl Paraben: Structural Relationships and Relative Energy Differences

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