Molecular and crystal structures of 4-acylphenyl 4′-alkyloxybenzoates

Effects of alkylthio groups on phase transitions of organic molecules and liquid crystals: a comparative study with alkyl and alkoxy groups

“…Overall, the crystal structures of the three shortest methylthio-based molecules indicated several contacts, which however differed largely depending on respective molecules. This indicates that the attractive interactions from the polarizable sulfur atoms are reflected in spatially averaged phenomena such as dispersion forces, which should be, according to the literature, [2][3][4][83][84][85][86][87][88][89][90][91][92][93][94][95][96][97][98][99][100] distinguished from the directional non-covalent orbital bonds around sulfur atoms such as chalcogen bonds. For example, the directional, orbital, non-covalent chalcogen bonds (not transient incidental interatomic contact or collision) are often observed between chalcogen atoms (close or bound to electron withdrawing bonds) and electron rich sites (such as lone pairs and anions), which are more pronounced for heavier chalcogens selenium and tellurium.…”

“…The closest CO⋯H contacts attributed to the intermolecular hydrogen bonds are observed as with typical phenyl benzoates. [84][85][86][87] Examining the contacts around the sulfur atoms, S(1)⋯C( 5) contacts (3.691 Å) are indicated on the edges of the phenyl rings, which might stem from the S⋯π interactions. 9,10 Nonetheless, the S⋯C contacts on the edge of phenyl rings cannot practically be distinguished from the adjacent S⋯CO contacts.…”

“…In the molecular packings, the short CO⋯H contacts (2.466 Å) due to the hydrogen bonds were observed between not only fully overlapped molecules but also half-shifted packing moieties, as typically observed in phenyl benzoates. [84][85][86][87] In addition to the dominant CH⋯π and π⋯π interactions, these CO⋯H hydrogen bonds also likely have a significant role in the packing manners. The relatively similar half-shifted packing manner and hydrogen bond contacts were found also in the crystal structure of the methyl-substituted analogue (i.e., PBB-1) (CCDC No: 1265699).…”

“…2.48 Å) ascribed to the hydrogen bonds were observed, in contrast to PBB, PBB-1, and typical phenyl benzoates. [84][85][86][87][88][89] On the other hand, various interatomic contacts were indicated around the sulfur atoms. They implied the associated interactions, such as the S⋯HC hydrogen bonds [S(1)⋯H (10) and S(1)⋯H(4) distances of ca.…”

Crystal structure of 4-[(3-methylbut-3-enoyl)oxy]phenyl 4-n-hexyloxybenzoate

“…Upon a rise in temperature, melting starts from the loose aliphatic areas, whereas the aromatic areas retain their ordering over a certain time, resulting in mesophase formation. All these peculiarities have been observed in the crystal packing of alkyl-and alkyloxycyanobiphenyls (Kuz'mina & Kucherepa, 2011;Kuz'mina et al, 2012), alkyloxybenzoic acids (Kuz'mina et al, 2009), n-(alkyloxybenzilidene)-n 0 -tolyidines (Kuz'mina et al, 2016) and phenylbenzoates (Konstantinov et al, 2013;Kuz'mina et al, 2014), which represent a precursor of the mesophase.…”