Investigation of the conformation and hydrogen bonds in adamantylthiacalix[4]arene by IR spectroscopy and DFT

Furer, V.L.; Potapova, L.I.; Vatsouro, Ivan; Ковалев, В. В.; Shokova, E. A.; Коваленко, В. И.

doi:10.1016/j.molstruc.2018.06.008

Cited by 6 publications

(2 citation statements)

References 26 publications

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“…An exhausting search of conformal configurations of Calix [4]arene derivatives including acryloyl moiety is the main promise of this work. Exclusively, compound 4 aside from others, the exact conformation could not be determined exactly by experimental methods (NMR or IR) since there is no -OH group being capable of intra- (2) : stabilization energy, b Energy difference of i (donor) and j (acceptor) NBO orbitals, c Fij: the Fock matrix element. ∆E: E LUMO -E HOMO , χ :Electronegativity, µ:Chemical potential, η:Chemical hardness, σ:Global softness, ω :Electrophilicity index molecular hydrogen bonding.…”

Section: Resultsmentioning

confidence: 99%

Computational Insight into Conformational Rearrangement and Intramolecular-H Bond Analysis of Some Calix[4]Arenes Including Acryloyl Moiety

Karayel

2019

Hittite J. Sci. Eng.

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C alixarenes are macrocyclic compounds, which are utilized in important fields like pharmacy, engineering and medicine. They are applied as sensors in various areas of human activities, in medical applications and environmental protection (1, 2). Moreover, they are used in catalysis as well as in molecular recognition. Their cage-like structures play important role in host-guest mechanism in supramolecular chemistry (1, 2). In addition, the functionalization of Calixarenes by means of substituting methylene bridges with heteroatoms is quite important in order to discover new compounds (1, 2). Calixarenes attract much attention due to the rich conformational possibilities which come in four varieties: Cone, Partial Cone, 1,2-Alternate and 1,3-Alternate (3-6). The four forms of Calixarenes are mainly due to the free rotation of methylene groups. The determination of stable conformations could not always be achieved correctly by spectroscopic techniques such as IR and NMR. On the other hand, the current state of theory on predicting Calixerarene derivatives remains inconclusive or insufficient (7) hence there is still need for extensive theoretical work. Moreover, in literature, it has been highlighted that the determination of the conformational stability from experimental results of Calixarenes

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Section: Resultsmentioning

confidence: 99%

Computational Insight into Conformational Rearrangement and Intramolecular-H Bond Analysis of Some Calix[4]Arenes Including Acryloyl Moiety

Karayel

2019

Hittite J. Sci. Eng.

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“…Earlier, we showed that thiacalix [4]arenes with large adamantyl substituents are in the cone conformation [9,10]. It is known that carboxylic acids form dimers via H-bonds [11].…”

Section: Introductionmentioning

confidence: 98%

Study of IR spectra of thiacalix[4]arene with carboxyl and adamantyl groups

et al. 2021

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The IR spectra of p-(3-carboxy-1-adamantyl)thiacalix[4]arene (1) were studied. IR spectra of compound 1 do not contain bands of free hydroxyl groups. The νOH value at 3377 cm-1 signifies the formation of an intramolecular H-bond along the lower edge of compound 1. It was found that all the studied calixarene derivatives containing adamantylcarboxylic acid fragments on the upper edge form H-bonds between adjacent carboxyl groups. At the top edge of thiacalixarene, carboxyl groups form dimers or cyclic tetramers through intramolecular H-bonds. The conformation of the cone is preserved, but there is a mutual influence of Hbonds along the lower and upper edges of the thiacalixarene molecules. A structure with dimeric H-bonds between carboxyl groups is 1.5 kJ/mol less preferable than the conformation with tetrameric cyclic H-bonds of compound 1. Comparison of the νOH absorption frequency of alcohol hydroxyl groups in IR spectra of thiacalixarenes shows that the presence of the second H-bond system weakens the H-bonds of alcohol hydroxyl groups slightly.

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Experimental and DFT investigation of structure and IR spectra of H-bonded associates of p-(3-carboxy-1-adamantyl)thiacalix[4]arene

et al. 2021

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Investigation of the conformation and hydrogen bonds in adamantylthiacalix[4]arene by IR spectroscopy and DFT

Cited by 6 publications

References 26 publications

Computational Insight into Conformational Rearrangement and Intramolecular-H Bond Analysis of Some Calix[4]Arenes Including Acryloyl Moiety

Computational Insight into Conformational Rearrangement and Intramolecular-H Bond Analysis of Some Calix[4]Arenes Including Acryloyl Moiety

Study of IR spectra of thiacalix[4]arene with carboxyl and adamantyl groups

Experimental and DFT investigation of structure and IR spectra of H-bonded associates of p-(3-carboxy-1-adamantyl)thiacalix[4]arene

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