Crystal structures of 2-acetyl-4-ethynylphenol and 2-acetyl-4-(3-hydroxy-3-methylbut-1-yn-1-yl)phenol

Hübscher, Jörg; Rosin, Robert; Seichter, Wilhelm; Weber, Edwin

doi:10.1107/s2056989016013451

Acta Cryst E

2016

DOI: 10.1107/s2056989016013451

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Crystal structures of 2-acetyl-4-ethynylphenol and 2-acetyl-4-(3-hydroxy-3-methylbut-1-yn-1-yl)phenol

Jörg Hübscher

Robert Rosin

Wilhelm Seichter

et al.

Abstract: Crystal structures of two 4-substituted derivatives of 2-acetylphenol are discussed comparatively with reference to modes of hydrogen bonding.

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2-Methyl-4-(4-nitrophenyl)but-3-yn-2-ol: crystal structure, Hirshfeld surface analysis and computational chemistry study

Caracelli¹,

Zukerman-Schpector²,

Schwab³

et al. 2019

Acta Cryst E

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The di-substituted acetylene residue in the title compound, C11H11NO3, is capped at either end by di-methylhydroxy and 4-nitrobenzene groups; the nitro substituent is close to co-planar with the ring to which it is attached [dihedral angle = 9.4 (3)°]. The most prominent feature of the molecular packing is the formation, via hydroxy-O—H...O(hydroxy) hydrogen bonds, of hexameric clusters about a site of symmetry \overline{3}. The aggregates are sustained by 12-membered {...OH}6 synthons and have the shape of a flattened chair. The clusters are connected into a three-dimensional architecture by benzene-C—H...O(nitro) interactions, involving both nitro-O atoms. The aforementioned interactions are readily identified in the calculated Hirshfeld surface. Computational chemistry indicates there is a significant energy, primarily electrostatic in nature, associated with the hydroxy-O—H...O(hydroxy) hydrogen bonds. Dispersion forces are more important in the other identified but, weaker intermolecular contacts.

show abstract

2-Methyl-4-(4-nitrophenyl)but-3-yn-2-ol: crystal structure, Hirshfeld surface analysis and computational chemistry study

Caracelli¹,

Zukerman-Schpector²,

Schwab³

et al. 2019

Acta Cryst E

View full text Add to dashboard Cite

show abstract

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Crystal structures of 2-acetyl-4-ethynylphenol and 2-acetyl-4-(3-hydroxy-3-methylbut-1-yn-1-yl)phenol

Abstract: Crystal structures of two 4-substituted derivatives of 2-acetylphenol are discussed comparatively with reference to modes of hydrogen bonding.

Cited by 1 publication

References 22 publications

2-Methyl-4-(4-nitrophenyl)but-3-yn-2-ol: crystal structure, Hirshfeld surface analysis and computational chemistry study

2-Methyl-4-(4-nitrophenyl)but-3-yn-2-ol: crystal structure, Hirshfeld surface analysis and computational chemistry study

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Crystal structures of 2-acetyl-4-ethynylphenol and 2-acetyl-4-(3-hydroxy-3-methylbut-1-yn-1-yl)phenol

Abstract: Crystal structures of two 4-substituted derivatives of 2-acetyl­phenol are discussed comparatively with reference to modes of hydrogen bonding.

Cited by 1 publication

References 22 publications

2-Methyl-4-(4-nitrophenyl)but-3-yn-2-ol: crystal structure, Hirshfeld surface analysis and computational chemistry study

2-Methyl-4-(4-nitrophenyl)but-3-yn-2-ol: crystal structure, Hirshfeld surface analysis and computational chemistry study

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Abstract: Crystal structures of two 4-substituted derivatives of 2-acetylphenol are discussed comparatively with reference to modes of hydrogen bonding.