Boron Trifluoride Catalyzed Esterification of <i>p</i>-Aminosalicylic Acid

Schaefer, Joseph J.; Doub, Leonard

doi:10.1021/ja01178a529

Cited by 8 publications

(2 citation statements)

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“…The alkylation process has gained popularity and is being applied in laboratories and in some cases in industry. While reports of the esterification of carboxylic acids catalysed by BTE are known and take place in the presence of an alcohol [19][20][21], the alkylation of carboxylic acids by an ethyl moiety of BTE in the absence of ethyl alcohol from the reaction system is unexpected and to the best of our knowledge has not been reported and therefore forms the basis of this communication.…”

Section: Introductionmentioning

confidence: 93%

Unprecedented alkylation of carboxylic acids by boron trifluoride etherate

Jumbam¹,

Maganga²,

Masamba³

et al. 2018

Bull. Chem. Soc. Eth.

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The alkylation of carboxylic acids by an ethyl moiety of boron trifluoride etherate in the absence of ethyl alcohol from the reaction system is unexpected and novel. Both aromatic and aliphatic carboxylic acids were clearly alkylated affording good yields in short reaction times with the exception of nicotinic acid that necessitated an overnight reaction. It was noted that while ortho-substituted hydroxyl groups of carboxylic acids investigated were not affected by alkylation, those of meta-and para-substituted carboxylic acids were partially etherified. Furthermore, the alkylation reaction was found to be compatible with a range of functional groups such as halogens, amino and nitro groups except for the alkene function of undecylenic acid that underwent polymerisation with concomitant alkylation of its carboxylic acid function.

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Section: Introductionmentioning

confidence: 93%

Unprecedented alkylation of carboxylic acids by boron trifluoride etherate

Jumbam¹,

Maganga²,

Masamba³

et al. 2018

Bull. Chem. Soc. Eth.

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“…From the perspective of its reaction in the gas phase, representative examples of such studies include its reaction with (i) catecholate and related anions [2], (ii) the gas phase ion chemistry of BF 3 /CH 4 mixtures [3], and (iii) the reaction of ammonia and methylamine [4,5]. From the perspective of the reactions of BF 3 in solution (where it is often used in the form of its etherate adduct), it has been shown to play a role in facilitating various polymerization reactions [6][7][8], dehydration reactions of alcohols [9,10], esterification reactions [11][12][13], alkylation reactions [14,15], as well as the synthesis of syn-fluorohydrins from epoxides [16]. It has also been reported that triplet diphenylcarbene could be inserted into the B-F bond of BF 3 [17].…”

Section: Introductionmentioning

confidence: 99%

A Systematic Exploration of B–F Bond Dissociation Enthalpies of Fluoroborane-Type Molecules at the CCSD(T)/CBS Level

O'Reilly

Karton

2023

Molecules

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Fluoroborane-type molecules (R1R2B–F) are of interest in synthetic chemistry, but to date, apart from a handful of small species (such as H2BF, HBF2, and BF3), little is known concerning the effect of substituents in governing the strength of the B–F bonds of such species toward homolytic dissociation in the gas phase. In this study, we have calculated the bond dissociation enthalpies (BDEs) of thirty unique B–F bonds at the CCSD(T)/CBS level using the high-level W1w thermochemical protocol. The B–F bonds in all species considered are very strong, ranging from 545.9 kJ mol−1 in (H2B)2B–F to 729.2 kJ mol−1 HBF2. Nevertheless, these BDEs still vary over a wide range of 183.3 kJ mol−1. The structural properties that affect the BDEs are examined in detail, and the homolytic BDEs are rationalized based on molecule stabilization enthalpies and radical stabilization enthalpies. Since polar B–F bonds may represent a challenging test case for density functional theory (DFT) methods, we proceed to examine the performance of a wide range of DFT methods across the rungs of Jacob′s Ladder for their ability to compute B–F BDEs. We find that only a handful of DFT methods can reproduce the CCSD(T)/CBS BDEs with mean absolute deviations (MADs) below the threshold of chemical accuracy (i.e., with average deviations below 4.2 kJ mol−1). The only functionals capable of achieving this feat were (MADs given in parentheses): ωB97M-V (4.0), BMK (3.5), DSD-BLYP (3.8), and DSD-PBEB95 (1.8 kJ mol−1).

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New Compounds: Convenient Selective Esterification of Aromatic Carboxylic Acids Bearing Other Reactive Groups Using a Boron Trifluoride Etherate—Alcohol Reagent

Kadaba

1974

Journal of Pharmaceutical Sciences

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Boron Trifluoride Catalyzed Esterification of p-Aminosalicylic Acid

Cited by 8 publications

References 0 publications

Unprecedented alkylation of carboxylic acids by boron trifluoride etherate

Unprecedented alkylation of carboxylic acids by boron trifluoride etherate

A Systematic Exploration of B–F Bond Dissociation Enthalpies of Fluoroborane-Type Molecules at the CCSD(T)/CBS Level

New Compounds: Convenient Selective Esterification of Aromatic Carboxylic Acids Bearing Other Reactive Groups Using a Boron Trifluoride Etherate—Alcohol Reagent

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