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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

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

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Caracelli, Ignez [1] ; Zukerman-Schpector, Julio [2] ; Schvvab, Ricardo S. [2] ; da Silva, Everton M. [2] ; Jotani, Mukesh M. [3] ; Tiekink, Edward R. T. [4]
Total Authors: 6
[1] Univ Fed Sao Carlos, Dept Fis, BR-13565905 Sao Carlos, SP - Brazil
[2] Univ Fed Sao Carlos, Dept Quim, BR-13565905 Sao Carlos, SP - Brazil
[3] Bhavans Sheth RA Coll Sci, Dept Phys, Ahmadabad 380001, Gujarat - India
[4] Sunway Univ, Res Ctr Crystalline Mat, Sch Sci & Technol, Bandar Sunway 47500, Selangor Darul - Malaysia
Total Affiliations: 4
Document type: Journal article
Web of Science Citations: 0

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)degrees]. The most prominent feature of the molecular packing is the formation, via hydroxy-O-H center dot center dot center dot O(hydroxy) hydrogen bonds, of hexameric clusters about a site of symmetry (3) over bar. The aggregates are sustained by 12-membered [center dot center dot center dot OH](6) synthons and have the shape of a flattened chair. The clusters are connected into a three-dimensional architecture by benzene-C-H center dot center dot center dot 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 center dot center dot center dot O(hydroxy) hydrogen bonds. Dispersion forces are more important in the other identified but, weaker intermolecular contacts. (AU)

FAPESP's process: 14/50249-8 - Green chemistry: sustainable synthetic methods employing benign solvents, safer reagents, and bio-renewable feedstock
Grantee:Arlene Gonçalves Corrêa
Support type: Research Grants - Research Centers in Engineering Program
FAPESP's process: 13/06558-3 - Asymmetric catalysis: preparation of chiral alcohols and their derivatives from highly functionalized organozinc reagents and application of new chiral ligands supported on magnetic nanoparticles
Grantee:Ricardo Samuel Schwab
Support type: Regular Research Grants