Proton Transfer in Homodimers of Carboxylic Acids: The Rotational Spectrum of the Dimer of Acrylic Acid

2012 ◽  
Vol 134 (46) ◽  
pp. 19281-19286 ◽  
Author(s):  
Gang Feng ◽  
Laura B. Favero ◽  
Assimo Maris ◽  
Annalisa Vigorito ◽  
Walther Caminati ◽  
...  
Keyword(s):  
Acrylic Acid ◽  
Proton Transfer ◽  
Carboxylic Acids ◽  
Rotational Spectrum

Molecular Cocrystals of Carboxylic Acids. XXXII The Crystal Structures of the Adducts of 2-Aminobenzothiazole with 3,5-Dinitrobenzoic Acid (Adduct Hydrate) and 3-Aminobenzoic Acid, and 2-Amino-2-thiazoline with 2-Aminobenzoic Acid

1998 ◽  
Vol 51 (7) ◽  
pp. 587 ◽  
Author(s):  
Daniel E. Lynch ◽  
Graham Smith ◽  
Karl A. Byriel ◽  
Colin H. L. Kennard
Keyword(s):  
Optical Properties ◽  
Proton Transfer ◽  
Crystal Structures ◽  
Carboxylic Acids ◽  
Second Order ◽  
Aminobenzoic Acid ◽  
Aromatic Carboxylic Acids ◽  
X Ray ◽  
Linear Optical Properties ◽  
Acid Adduct

Two adducts of 2-aminobenzothiazole and one of 2-amino-2-thiazoline with aromatic carboxylic acids have been synthesized and their X-ray crystal structures determined. These are 2-aminobenzothiazole with 3,5-dinitrobenzoic acid (the 1 : 1 adduct hydrate) (1), and 3-aminobenzoic acid (1 : 1) (2), and 2-amino-2-thiazoline with 2-aminobenzoic acid (1 : 1) (3). Compound (1) is a non-centrosymmetric proton-transfer complex and gave a signal of 0·30 relative to urea when tested for second-order non-linear optical properties. Compound (3) is also a proton-transfer complex but (2) is not.

Solvent-mediated pseudo-quadruple hydrogen-bond motifs in three lamotrigine–carboxylic acid complexes

2013 ◽  
Vol 69 (10) ◽  
pp. 1164-1169 ◽  
Author(s):  
Balasubramanian Sridhar ◽  
Jagadeesh Babu Nanubolu ◽  
Krishnan Ravikumar
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Carboxylic Acid ◽  
Proton Transfer ◽  
Antiepileptic Drug ◽  
Carboxylic Acids ◽  
Solvent Interactions ◽  
Partial Transfer ◽  
Quadruple Hydrogen Bonding ◽  
Quadruple Hydrogen Bond

Lamotrigine, an antiepileptic drug, has been complexed with three aromatic carboxylic acids. All three compounds crystallize with the inclusion ofN,N-dimethylformamide (DMF) solvent,viz.lamotriginium [3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium] 4-iodobenzoateN,N-dimethylformamide monosolvate, C9H8Cl2N5+·C7H4IO2−·C3H7NO, (I), lamotriginium 4-methylbenzoateN,N-dimethylformamide monosolvate, C9H7Cl2N5+·C8H8O2−·C3H7NO, (II), and lamotriginium 3,5-dinitro-2-hydroxybenzoateN,N-dimethylformamide monosolvate, C9H8Cl2N5+·C7H3N2O7−·C3H7NO, (III). In all three structures, proton transfer takes place from the acid to the lamotrigine molecule. However, in (I) and (II), the acidic H atom is disordered over two sites and there is only partial transfer of the H atom from O to N. In (III), the corresponding H atom is ordered and complete proton transfer has occurred. Lamotrigine–lamotrigine, lamotrigine–acid and lamotrigine–solvent interactions are observed in all three structures and they thereby exhibit isostructurality. The DMF solvent extends the lamotrigine–lamotrigine dimers into a pseudo-quadruple hydrogen-bonding motif.

A kinetic investigation of the effects of molecular complexing on the acidities of some π donor carboxylic acids

1977 ◽  
Vol 55 (6) ◽  
pp. 1028-1038 ◽  
Author(s):  
Allan K. Colter ◽  
R. James Kersting
Keyword(s):  
Carboxylic Acid ◽  
Acrylic Acid ◽  
Carboxylic Acids ◽  
Rate Constants ◽  
Association Constants ◽  
Second Order ◽  
Kinetic Investigation ◽  
Rate Data ◽  
Dihydroxybenzoic Acid ◽  
Order Rate

Rates of reaction of the five π donor acids indole-3-acrylic acid (IAA), indole-5-carboxylic acid (ICA), 3,4,5-trimethoxybenzoic acid (TMBA), 2,4-dihydroxybenzoic acid (DHBA), and 3,4,5-trihydroxybenzoic acid (THBA) with 4-chlorodiphenyldiazomethane (4-ClDDM) in ethanol at 30 °C were measured in the presence of the π acceptors 1,3,5-trinitrobenzene (TNB), benzotrifuroxan (BTF), and 1,2,4,5-tetracyanobenzene (TCNB) and in the absence of acceptor. For 12 of the 13combinations studied, added acceptor produced rate enhancements. The rate data were combined with independently-determined 1:1 acceptor – donor acid association constants to obtain second-order rate constants for reaction of the 1:1 acceptor – donor acid complexes. From the increase in the rate constant resulting from complexation, estimates of the increase in Ka(H2O, 25 °C) produced by complexation were obtained for 13 acceptor – donor acid combinations. Second-order rate constants for reaction of 4-ClDDM with 10 other carboxylic acids and p-toluenesulfonic acid in ethanol at 30°C were also measured and the pattern of reactivity shown to parallel very closely that of diphenyldiazomethane.

Facile Syntheses and Studies of 8-Substituted-4-(4-tert-butylphenyl/ 4-acetamidophenyl)-2,3-dihydro-1,5-benzothiazepine-2-carboxylic Acids

2020 ◽  
Vol 5 (1) ◽  
pp. 40-44
Author(s):  
Seema Pant
Keyword(s):  
Escherichia Coli ◽  
Staphylococcus Aureus ◽  
Candida Albicans ◽  
Acrylic Acid ◽  
Carboxylic Acids ◽  
Analytical Data ◽  
Enterobacter Cloacae ◽  
Polymyxin B ◽  
Single Step ◽  
Reference Drug

Two series of new 8-substituted-4-(4-tert-butylphenyl)-2,3-dihydro-1,5-benzothiazepine-2-carboxylic acids and 8-substituted-4-(4-acetamidophenyl)-2,3-dihydro-1,5-benzothiazepine-2-carboxylic acids have been synthesized by Michael condensation of 5-substituted-2-aminobenzenethiols with β-(4- tert-butylbenzoyl) acrylic acid or β-(4-acetamidobenzoyl) acrylic acid, in ethanol in acidic medium in a single step, in 58-64 % yield. The structures of the newly synthesized compounds were confirmed by their IR, 1H NMR and mass spectral analyses and micro analytical data. They were screened for antimicrobial activity, against the Gram-positive bacteria, Staphylococcus aureus, Gram-negative bacteria, Enterobacter cloacae and Escherichia coli, with respective reference compounds, vancomycin, polymyxin B, colistin-polymyxin B and against the fungus, Candida albicans with reference drug fluconazole. Most of the compounds showed activity against Staphylococcus aureus, Enterobacter cloacae and fungus Candida albicans, while none of the compounds showed activity against Escherichia coli.

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