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5 pages, 620 KiB

Open AccessShort Note

by Diyana Dimitrova, Stanimir Manolov, Dimitar Bojilov, Iliyan Ivanov and Paraskev Nedialkov

Molbank 2024, 2024(2), M1802; https://doi.org/10.3390/M1802 - 1 Apr 2024

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Herein, we report the synthesis of N-(3-chlorophenethyl)-4-nitrobenzamide in the reaction between 2-(3-chlorophenyl)ethan-1-amine and 4-nitrobenzoyl chloride. The newly obtained bio-functional hybrid molecule was fully characterized via ¹H, ¹³C NMR, UV, and mass spectral data. Full article

(This article belongs to the Section Structure Determination)

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6 pages, 1027 KiB

Open AccessShort Note

N-(2,2-Diphenylethyl)-4-nitrobenzamide

by Diyana Dimitrova, Stanimir Manolov, Iliyan Ivanov, Dimitar Bojilov, Lyusi Kasamova and Paraskev Nedialkov

Molbank 2024, 2024(1), M1775; https://doi.org/10.3390/M1775 - 12 Feb 2024

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Abstract

In this study, we outline the eco-friendly mechanosynthesis of N-(2,2-diphenylethyl)-4-nitrobenzamide by reacting 2,2-diphenylethan-1-amine with 4-nitrobenzoyl chloride. The resulting bio-functional hybrid compound was meticulously characterized through the analysis of ¹H-, ¹³C-NMR, UV, and detailed mass spectral analysis. Full article

(This article belongs to the Section Structure Determination)

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12 pages, 2411 KiB

Open AccessArticle

The Effect of the ortho Nitro Group in the Solvolysis of Benzyl and Benzoyl Halides

by Kyoung-Ho Park, Chan Joo Rhu, Jin Burm Kyong and Dennis N. Kevill

Int. J. Mol. Sci. 2019, 20(16), 4026; https://doi.org/10.3390/ijms20164026 - 18 Aug 2019

Cited by 6 | Viewed by 3296

Abstract

A kinetic study was carried out on the solvolysis of o-nitrobenzyl bromide (o-isomer, 1) and p-nitrobenzyl bromide (p-isomer, 3), and o-nitrobenzoyl chloride (o-isomer, 2) in a wide range of solvents under various temperatures. In all of the solvents without aqueous fluoroalcohol, the reactions of 1 were solvolyzed at a similar rate to those observed for 3, and the reaction rates of 2 were about ten times slower than those of the previously studied p-nitrobenzoyl chloride (p-isomer, 4). For solvolysis in aqueous fluoroalcohol, the reactivity of 2 was kinetically more reactive than 4. The l/m values of the extended Grunwald–Winstein (G–W) equation for solvolysis of 1 and 2 in solvents without fluoroalcohol content are all significantly larger than unity while those in all the fluoroalcohol solvents are less than unity. The role of the ortho-nitro group as an intramolecular nucleophilic assistant (internal nucleophile) in the solvolytic reaction of 1 and 2 was discussed. The results are also compared with those reported earlier for o-carbomethoxybenzyl bromide (5) and o-nitrobenzyl p-toluenesulfonate (7). From the product studies and the activation parameters for solvolyses of 1 and 2 in several organic hydroxylic solvents, mechanistic conclusions are drawn. Full article

(This article belongs to the Special Issue Solution Chemical Kinetics 2.0)

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23 pages, 1460 KiB

Open AccessArticle

Calculated Third Order Rate Constants for Interpreting the Mechanisms of Hydrolyses of Chloroformates, Carboxylic Acid Halides, Sulfonyl Chlorides and Phosphorochloridates

by T. William Bentley

Int. J. Mol. Sci. 2015, 16(5), 10601-10623; https://doi.org/10.3390/ijms160510601 - 8 May 2015

Cited by 9 | Viewed by 7585

Abstract

Hydrolyses of acid derivatives (e.g., carboxylic acid chlorides and fluorides, fluoro- and chloroformates, sulfonyl chlorides, phosphorochloridates, anhydrides) exhibit pseudo-first order kinetics. Reaction mechanisms vary from those involving a cationic intermediate (S_N1) to concerted S_N2 processes, and further to third order reactions, in which one solvent molecule acts as the attacking nucleophile and a second molecule acts as a general base catalyst. A unified framework is discussed, in which there are two reaction channels—an S_N1-S_N2 spectrum and an S_N2-S_N3 spectrum. Third order rate constants (k₃) are calculated for solvolytic reactions in a wide range of compositions of acetone-water mixtures, and are shown to be either approximately constant or correlated with the Grunwald-Winstein Y parameter. These data and kinetic solvent isotope effects, provide the experimental evidence for the S_N2-S_N3 spectrum (e.g., for chloro- and fluoroformates, chloroacetyl chloride, p-nitrobenzoyl p-toluenesulfonate, sulfonyl chlorides). Deviations from linearity lead to U- or V-shaped plots, which assist in the identification of the point at which the reaction channel changes from S_N2-S_N3 to S_N1-S_N2 (e.g., for benzoyl chloride). Full article

(This article belongs to the Special Issue Solution Chemical Kinetics)

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21 pages, 196 KiB

Open AccessArticle

Preparation, GIAO NMR Calculations and Acidic Properties of Some Novel 4,5-dihydro-1H-1,2,4-triazol-5-one Derivatives with Their Antioxidant Activities

by Haydar Yüksek, Muzaffer Alkan, Ismail Cakmak, Zafer Ocak, Şule Bahçeci, Mustafa Calapoğlu, Mahfuz Elmastaş, Ali Kolomuç and Havva Aksu

Int. J. Mol. Sci. 2008, 9(1), 12-32; https://doi.org/10.3390/ijms9010012 - 8 Jan 2008

Cited by 12 | Viewed by 11674

Abstract

Six novel 3-alkyl(aryl)-4-(p-nitrobenzoylamino)-4,5-dihydro-1H-1,2,4-triazol-5- ones (2a-f) were synthesized by the reactions of 3-alkyl(aryl)-4-amino-4,5-dihydro-1H- 1,2,4-triazol-5-ones (1a-f) with p-nitrobenzoyl chloride and characterized by elemental analyses and IR, ¹H-NMR, ¹³C-NMR and UV spectral data. The newly synthesized compounds 2 were titrated potentiometrically with tetrabutylammonium hydroxide in four non-aqueous solvents such as acetone, isopropyl alcohol, tert-butyl alcohol and N,Ndimethylformamide, and the half-neutralization potential values and the corresponding pKa values were determined for all cases. Thus, the effects of solvents and molecular structure upon acidity were investigated. In addition, isotropic ¹H and ¹³C nuclear magnetic shielding constants of compounds 2 were obtained by the gauge-including-atomic-orbital (GIAO) method at the B3LYP density functional level. The geometry of each compound has been optimized using the 6-311G basis set. Theoretical values were compared to the experimental data. Furthermore, these new compounds and five recently reported 3-alkyl-4-(2- furoylamino)-4,5-dihydro-1H-1,2,4-triazol-5-ones (3a-c,e,f) were screened for their antioxidant activities. Full article

(This article belongs to the Section Physical Chemistry, Theoretical and Computational Chemistry)

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2 pages, 93 KiB

Open AccessShort Note

3-[5-(tert-Butyldimethylsilyloxy)-3-p-nitrobenzoyl-1-oxo- 2-(phenylmethoxy)hexyl]-4-(phenylmethyl)-2-oxazolidinone

by Margaret A. Brimble and Josephine S. O. Park

Molecules 2000, 5(2), M135; https://doi.org/10.3390/M135 - 23 Feb 2000

Viewed by 3284

Abstract

A mixture of alcohol 1 (121 mg, 0.23 mmol) [1], triethylamine (48 l, 0.34 mmol) and p-nitrobenzoyl chloride (51 mg, 0.28 mmol) in dichloromethane (2 ml) was stirred for 2 h. at 30ºC.[...] Full article

(This article belongs to the Section Molbank Section of Molecules, 1997-2001)

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