ArticleJournal of molecular spectroscopy2017
Amine vs. carboxylic acid protonation in ortho-, meta-, and para-aminobenzoic acid: An IRMPD spectroscopy study.
Article in Journal of molecular spectroscopy, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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7 citing papers in PubMed, 53 citations in OpenAlex.
- Therapeutic potential of [(8-hydroxyquinolin-7-yl)(phenyl)methylamino] benzoic acid regioisomers against human-intoxicating botulinum neurotoxin serotypes: computational modeling to in vivo protection.Journal of computer-aided molecular design · 2026Article
- Three Candidates, Two Peaks: Addressing Conflicting Assignments of Fentanyl Protomers with DMS-UVPD.Journal of the American Society for Mass Spectrometry · 2025Article
- Isomers and band assignments in the cryogenic vibrational spectrum of the binary complex between water and protonated formic acid using two color, IR-IR photobleaching and H/D isotopic substitution.The Journal of chemical physics · 2025Article
- The immunomodulatory effects of vitamins in cancer.Frontiers in immunology · 2024Review
- Novel Para-Aminobenzoic Acid Analogs and Their Potential Therapeutic Applications.Biomedicines · 2023Review
- Vibrational spectroscopy of the cryogenically cooled O- and N-protomers of 4-Aminobenzoic acid: Tag effects, isotopic labels, and identification of theInternational journal of mass spectrometry · 2020Article
- Untrapping Kinetically Trapped Ions: The Role of Water Vapor and Ion-Source Activation Conditions on the Gas-Phase Protomer Ratio of Benzocaine Revealed by Ion-Mobility Mass Spectrometry.Journal of the American Society for Mass Spectrometry · 2017Article
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
Infrared multiple photon dissociation (IRMPD) spectroscopy and computational chemistry are applied to the ortho-, meta-, and para- positional isomers of aminobenzoic acid to investigate whether the amine or the carboxylic acid are the favored sites of proton attachment in the gas phase. The NH and OH stretching modes yield distinct patterns that establish the carboxylic acid as the site of protonation in para-aminobenzoic acid, as opposed to the amine group in ortho- and meta-aminobenzoic acid, in agreement with computed thermochemistries. The trends for para- and meta-substitutions can be rationalized simplistically by inductive effects and resonant stabilization, and will be discussed in light of computed charge distributions based from electrostatic potentials. In ortho-aminobenzoic acid, the close proximity of the amine and acid groups allow a simultaneous interaction of the proton with both groups, thus stabilizing and delocalizing the charge more effectively, and compensating for some of the resonance stabilization effects.
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