.beta.-Adrenoceptor studies. 5. Proton NMR and IR spectroscopic analysis of the conformation of the hydrohalide salts of .beta.-adrenoceptor-blocking aryloxypropanolamines. Evidence for a seven-membered ring structure with participation of two hydrogen bonds

Zaagsma, Johan

doi:10.1021/jm00190a017

Cited by 21 publications

(4 citation statements)

References 9 publications

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“…Chloride ion is in fact considered a hydrogen bond acceptor from a number of molecular groups, in particular from OH and NH [8][9][10]. The values found for d(H C •••Cl − ) and for <(O 3 H 2 Cl − ) indicate the existence of a favourable hydrogen bond direction compared with the value given in the surveys delivered by some authors [11,12]. The electrostatic interaction between the two ions takes place through the H A atom.…”

Section: Although the Value Of D(hmentioning

confidence: 71%

“…Cl − , the isopropilamine-2-propanol moiety in BTH results from that of BT by a rotation around the (C 3 -C 2 ) bond. The type of structure just described for the relaxed isolated molecule was also found in crystalline BTH [5] and was put forward to interpret the results obtained by 1 H NMR and IR spectroscopy for hydrohalide salts of ␤-blockers dissolved in aprotic non-polar solvents [12].…”

Section: Although the Value Of D(hmentioning

confidence: 98%

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Infrared study of the acidic and basic forms of betaxolol

Canotilho

Castro

Helena

et al. 2006

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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Betaxolol and its respective hydrochloride salt were studied in solution by computational calculations and infrared spectroscopy. The solution molecular conformations were taken to be the same as those exhibited by the compounds in the solid state given by X-ray diffraction and calculated after full geometry optimization by ab initio Hartree-Fock methods using the 6-31G(d) basis set. Infrared spectra of carbon tetrachloride solutions provide valuable information on the structure of the compounds in non-polar solvents at different concentrations.

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Section: Although the Value Of D(hmentioning

confidence: 71%

Section: Although the Value Of D(hmentioning

confidence: 98%

Infrared study of the acidic and basic forms of betaxolol

Canotilho

Castro

Helena

et al. 2006

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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show abstract

“…These compounds invariably prefer (the present structure is the first known exception) a simultaneous hydrogen bonding of OH and N+H moieties to the common C1-anion, thus forming a seven-membered ring system. Such an interaction has also been shown to exist in solution (Zaagsma, 1979).…”

mentioning

confidence: 85%

Structure of propyl 3-acetyl-4-[2-hydroxy-3-(isopropylamino)propoxy]carbanilate hydrochloride

Kettmann¹,

Csöllei²,

Ječný³

1992

Acta Crystallogr C

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“…The third point of interest in the present structure is the mode of interaction of cation (I) with the fumarate dianion since the carboxylate group of Asp 113 of the receptor is generally believed to act as a counterion for the positively charged amine of both agonists and antagonists (Strader, Sigal, Candelore, Rands, Hill & Dixon, 1988, and references therein). Previous studies on the hydrochloride salts of many adrenergic ligands not containing aromatic hydroxyl(s) (as competing hydrogen-bond donors) have shown that these cations, both in the solid state and in solution, prefer simultaneous hydrogen bonding of the OH and N+H groups to the common C1anion, thus forming a seven-membered ring (Kettmann & Cs611ei, 1989, and references therein;Zaagsma, 1979). Nonetheless, the present structure © 1991 International Union of Crystallography (2) 3.58 C (5) 2162 (3) 9173 (2) 1935 (2) 3.75 C (6) 2073 (3) 8140 (2) 2428 (2) 3-40 C (7) 2277 (3) 6011 (3) 3383 (2) 3.58 C (8) 2583 (3) 4697 (2) 3663 (1) 3.06 C(9) 4163 (3) 4216 (3) 3268 (2) 3.40 C(10) 5864 (3) 2283 (3) 3258 (2) 3.93 C(I 1)…”

mentioning

confidence: 99%