Crystal structure and inclusion property of p-tert-butylthiacalix[6]arene

Iki, Nobuhiko; Morohashi, Naoya; Suzuki, Tomohiro; Ogawa, Shuntaro; Aono, Mitsuru; Kabuto, Chizuko; Kumagai, Hitoshi; Takeya, H.; Miyanari, Setsuko; Miyano, Sotaro

doi:10.1016/s0040-4039(00)00211-2

Cited by 39 publications

(23 citation statements)

References 5 publications

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“…The ab initio methods of calculation, where geometry optimization is fulfilled in one approximation and the energy of a structure is calculated in another (in particular, at second order Möller Plesset level of theory), obviously slightly exaggerate the strength of H bonds in calix [4]arene; as a result, changes in H bond energy obtained by these methods approximate the value obtained by RHF/STO-2G. This tendency was also revealed in [25,26].…”

Section: Discussion Of Resultsmentioning

confidence: 88%

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Ab initio and density functional studies of cooperative hydrogen bonding in calix[4]-and calix[6]arenes

et al. 2006

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The cone conformation of 4 symmetry is shown by the Hartree-Fock method (3-21G basis) to be the predominant conformer of calix [4]arene; the compressed cone of 2 symmetry is the major conformer of calix [6] [7-9, 12, 13] and density functional [6-9, 14] methods, and only one work deals with investigation of calix [6]arenes by these methods [13]. None of these works dealing with calixarenes has reported on hydrogen bond energy calculations, although this energy is the key factor of conformational stability and conformational lability of calixarenes with free hydroxyl groups [12] and their reactivity [11].The stability of the hydrogen bond in calixarene was correlated with the reaction route involving this compound when dialkoxydihydroxycalix[4]arene was synthesized from monoalkoxytrihydroxycalix[4]arene [11] (Fig. 1). Similar alkylation and acylation reactions with intermediate phenoxide anions stabilized by the maximum number of stable hydrogen bonds were also reported for calixarenes having larger rings [11]. In his review [11] D. Rudkevich demonstrated in detail that intramolecular hydrogen bonds are as important as intermolecular hydrogen bonds for molecular void formation. Therefore further investigation of intramolecular hydrogen bonding in "guest-host" complexes (in particular, investigation of the energy parameters of hydrogen bonds) is of great importance in view of the influence of intramolecular hydrogen bonds on the route and rate of transformations involving cleavage and formation of covalent bonds and on the complexation ability of cavitands.I. I. Mechnikov Odessa National University; andrej_novikov@mail.ru, andrej_novikov@ukr.net.

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Section: Discussion Of Resultsmentioning

confidence: 88%

“…For calix [6]arenes, however, both theoretical and experimental investigations revealed three pairs of hydrogen bonds, which differ in their structural characteristics and are generally consistent with 2 molecular symmetry [26].…”

Section: Discussion Of Resultsmentioning

confidence: 92%

Ab initio and density functional studies of cooperative hydrogen bonding in calix[4]-and calix[6]arenes

et al. 2006

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“…Its form, with a metal-containing unit held between two calixarene ligands, is one commonly but not universally found in known thiacalixarene complexes. [20,30,[37][38][39][40][41][42][43][44][45][46] Here, one mononuclear formula unit, devoid of crystallographic symmetry, comprises the asymmet- ric unit of the structure, in which the two calixarene entities adopt cone conformations of near-fourfold symmetry (Table S1) and, phenolic hydrogen atoms having been refined, both appear to be singly deprotonated. Phenolic oxygen atoms O(111,131,141;221,231,241) are assigned as protonated on the basis of refinement of associated (x,y,z,U iso ) H ; in general H(mnl) are hydrogen-bonded to O[m(n -1)1].…”

Section: Ca(lh 3 ) 2 ·3dmf ϵ [(Dmf-o) 2 Ca(h 3 L)(h 3 L·dmf)] (1a)mentioning

confidence: 99%

Systematic Structural Coordination Chemistry ofp‐tert‐Butyltetrathiacalix[4]arene: Main Group Metal Complexes Other Than Those of Group 1

et al. 2010

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In extension of previous work involving structural characterisation of complex salts formed between main group 1 metal ions and p‐tert‐butyltetrathiacalixarene, LH4, the present study encompasses complexes with a wider array of main group 2, 13, 14 metal ions. For group 2, single‐crystal X‐ray structural characterisation of Ca(LH3)2·3dmf (1a), {Ca(LH2)·3dmf}2 (1b), Ba(LH3)2·6dmf (2a) and BaCO3·3Ba(LH3)2·3H2O·3CH3CN·12.25CH2Cl2 (2b) provides models for various coordination units. For group 13, this applies to {Ga(OH)(LH2)·3.5dmf}2 (3), {In(LH)·4EtOH·2CH2Cl2}2 (4a) and {In(OH)(LH2)·3CH2Cl2}4 (4b), and for group 14, to OPb4(LH)2·6dmf·dmso·2H2O (5). Overall, these define mononuclear (1a, 2a), binuclear (1b, 3, 4b) and tetranuclear (2b, 4b, 5) species. The calixarene cavities frequently include solvent molecules, though this capacity is clearly influenced by the nature of the bound metal ion(s) and their binding, as well as the associated impact on the conformation of the calixarene ligand(s).

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“…[13][14][15][16][17][18][19][20] These early reports pointed out the high complexation ability of thiacalixarene macrocycles. [16,17,21,22] This was then proved by the isolation and structural characterisation of complexes of p-tert-butylthiacalix [4]arene with Co II , [23,24] Ni II , [23] Cu II , [25] Zn II , [24,26] UO 2 , [27] Nd III , [28] and also with the alkali metals. [29] These complexes are either mononu-clear (UO 2 and Zn II ), [26,27] dinuclear (Co II and Ni II ), [23] trinuclear (Co II and Zn II ) [24] or tetranuclear (Cu II and Nd III ).…”

Section: Introductionmentioning

confidence: 99%

Tetra‐ and Decanuclear Iron(II) Complexes of Thiacalixarene Macrocycles: Synthesis, Structure, Mössbauer Spectroscopy and Magnetic Properties

et al. 2006

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Crystal structure and inclusion property of p-tert-butylthiacalix[6]arene

Cited by 39 publications

References 5 publications

Ab initio and density functional studies of cooperative hydrogen bonding in calix[4]-and calix[6]arenes

Ab initio and density functional studies of cooperative hydrogen bonding in calix[4]-and calix[6]arenes

Systematic Structural Coordination Chemistry ofp‐tert‐Butyltetrathiacalix[4]arene: Main Group Metal Complexes Other Than Those of Group 1

Tetra‐ and Decanuclear Iron(II) Complexes of Thiacalixarene Macrocycles: Synthesis, Structure, Mössbauer Spectroscopy and Magnetic Properties

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