Hydrogen Bonding in Diastereoisomeric Α-Β Aminoalcohols: A Reinvestigation of the Ephedrines by N.M.R

Hyne, J. B.

doi:10.1139/v60-013

Cited by 14 publications

(5 citation statements)

References 11 publications

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“…However, in the threo isomer la the intramolecular hydrogen bonding stabilizes the favored rotamer having minimum gauche interactions. This situation is similar to l/'-ephedrine (9) and irans-2-phenyl-3-methylmorpholine (10). Indeed a comparison of " and Jab of la and lb with l/'-ephedrine (9) and ephedrine (8) and trans-and cts-2-phenyl-3-10 methylmorpholines (10 and 11) shows a remarkable similarity between 1, 9, and 10, which have similar conformations (Table II).…”

supporting

confidence: 64%

Adrenoceptor blocking agents. 2. 2-(.alpha.-Hydroxyarylmethyl)-3,3-dimethylaziridines, a new class of selective .beta.2-adrenoceptor antagonists

Jain¹,

Khandelwal²,

Tripathi³

1978

J. Med. Chem.

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Threo- and erythro-2-(alpha-hydroxybenzyl)-3,3-dimethylaziridines (1a and 1b) and threo-2-[alpha-hydroxy(2-naphthyl)methyl]- and 2-[alpha-hydroxy(3,4-dichlorobenzyl)]-3,3-dimethylaziridines (1d and 1c) have been prepared as conformationally restricted analogues of beta-adrenoceptor blocking agents like dichloroisoproterenol (DCI) and pronethalol. The aziridine analogues 1 except possibly 1c are competitive antagonists of isoproterenol-induced response on a guinea pig tracheal chain preparation and the order of potency is 1d greater than 1a greater than or equal to 1b greater than propranolol greater than 1c. Unlike propranolol, these compounds have no effect on the isoproterenol-induced response on guinea pig auricles and no significant local anesthetic and antiarrhythmic activity. The aziridine analogues 1 represent the first of a new class of selective beta2-adrenoceptor blocking agents.

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supporting

confidence: 64%

Adrenoceptor blocking agents. 2. 2-(.alpha.-Hydroxyarylmethyl)-3,3-dimethylaziridines, a new class of selective .beta.2-adrenoceptor antagonists

Jain¹,

Khandelwal²,

Tripathi³

1978

J. Med. Chem.

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“…63 This is evidence of the presence in the compounds investigated of strong intramolecular hydrogen bonds the formation of which has been suggested also for diastereoisomeric a-and β-aminoalcohols 64 . An unusual intramolecular hydrogen bond between the hydroxyl proton and the oxygen of the methoxy-group has been observed in the study of solutions of substituted benzyl alcohols 85 .…”

Section: Alcoholsmentioning

confidence: 56%

Investigation of the Association of Alcohols and Phenols by the NMR Method

Brodskii¹,

Pokhodenko²,

Kuts³

1970

Russ. Chem. Rev.

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A.I.Brodskii (deceased), V.D.Pokhodenko, and V.S.KutsThe review discusses and analyses the literature on the study of the association of alcohols and phenols by the NMR method. The methods for the determination of the equilibrium constants and heats and entropies of formation of the association complexes of the above substances in both inert and basic solvents are described for equilibria of different types. The polar and steric effects of the substituents in alcohols and phenols on the thermodynamic functions for the formation of self-association complexes and also of association complexes with polar molecules has been analysed. The bibliography comprises 151 references. CONTENTS

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“…As temperature is increased the larger shift of the hydrazone signal to high field compared to that of the phenol is consistent with the former forming inter-and the latter intra-molecular hydrogen bonds. [57][58][59][60][61] The preference for the phenolic proton to form an intramolecular hydrogen bond to the imino nitrogen accords with solid state structures (see Figure 4). An exception is the 3-nitrosubstituted ligands where the nitro-group competes effectively for the phenolic proton to give structures such as those shown in Figure 6 (see also computational results below).…”

Section: Cumentioning

confidence: 68%

Salicylaldehyde Hydrazones: Buttressing of Outer-Sphere Hydrogen-Bonding and Copper Extraction Properties

et al. 2017

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Salicylaldehydes hydrazones are weaker copper extractants than their oxime derivatives which are used in hydrometallurgical processes to recover approximately 20% of the world's copper. Their strength, based on the extraction equilibrium constant Ke, can be increased by nearly three orders of magnitude by incorporating electron-withdrawing or hydrogen bond acceptor groups (X) ortho to the phenolic OH group of the salicylaldehyde unit. DFT calculations suggest that the effects of the 3-X substituents arise from a combination of their influence on the acidity of the phenol in the pHdependent equilibrium:and on their ability to "buttress" interligand hydrogen bonding by interacting with the hydrazone N-H donor group. X-ray crystal structure determination and computed structures indicated that in both the solid state and the gas phase, coordinated hydrazone groups are less planar than coordinated oximes and this has an adverse effect on intramolecular hydrogen bond formation to the neighbouring phenolate oxygen atoms.

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Hydrogen Bonding in Diastereoisomeric Α-Β Aminoalcohols: A Reinvestigation of the Ephedrines by N.M.R

Abstract: The results of a n n.m.r. study of the diastereoisomcric ephedrine and $-ephedrine ri~olecules in lion-polar sol\~ents are interpreted and discussed in t e r~n s of the relative stabilities of the intrarnolecularly hydrogen-bonded conformers.

Cited by 14 publications

References 11 publications

Adrenoceptor blocking agents. 2. 2-(.alpha.-Hydroxyarylmethyl)-3,3-dimethylaziridines, a new class of selective .beta.2-adrenoceptor antagonists

Adrenoceptor blocking agents. 2. 2-(.alpha.-Hydroxyarylmethyl)-3,3-dimethylaziridines, a new class of selective .beta.2-adrenoceptor antagonists

Investigation of the Association of Alcohols and Phenols by the NMR Method

Salicylaldehyde Hydrazones: Buttressing of Outer-Sphere Hydrogen-Bonding and Copper Extraction Properties

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