NMR Study of the Aminolysis of D‐Glycero‐D‐gulo‐heptono‐1,4‐lactone With <i>o</i> ‐Phenylenediamine Using Four Synthetic Methodologies

1D and 2D NMR spectra of amide 3 and benzimidazole 4 were unequivocally assigned. Moreover, the aminolysis of D-glycero-D-gulo-heptono-1,4-lactone 1 with o-phenylenediamine 2 was explored using different methodologies. Results indicated that focused ultrasound selectively yielded the amide 3. Studies demonstrated that intensive cavitation can exceed the activation energy without disrupting the thermodynamic equilibrium. Thus, the kinetic product (amide 3) was favored over the thermodynamic product (benzimidazole 4). In contrast, the ultrasonic cleaner led to an incomplete and unselective reaction. On the other hand, thermal induction favored the synthesis of benzimidazole 4, while the mechanochemical synthesis was inefficient in promoting the aminolysis of the γ-lactone 1 with compound 2.

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Publication Details

Journal
Magnetic Resonance in Chemistry
Published
2026-01-06
DOI
https://doi.org/10.1002/mrc.70081
Primary Topic
Ultrasound and Cavitation Phenomena
Type
article
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article

NMR Study of the Aminolysis of D‐Glycero‐D‐gulo‐heptono‐1,4‐lactone With o ‐Phenylenediamine Using Four Synthetic Methodologies

Eltonh Islas‐Trejo, Margarita Tlahuextl, Federico Javier Gaspar‐López, Luisa Fernanda Delgado‐Delgadillo et al.
Magnetic Resonance in Chemistry
Ultrasound and Cavitation Phenomena
article

NMR Study of the Aminolysis of D‐Glycero‐D‐gulo‐heptono‐1,4‐lactone With o ‐Phenylenediamine Using Four Synthetic Methodologies

Eltonh Islas‐Trejo, Margarita Tlahuextl, Federico Javier Gaspar‐López, Luisa Fernanda Delgado‐Delgadillo, Miguel Ángel García‐Ortiz, Antonio Rafael Tapia‐Benavides, Emmanuel Blas Patricio‐Rangel, Hugo Tlahuext
article en

Abstract

1D and 2D NMR spectra of amide 3 and benzimidazole 4 were unequivocally assigned. Moreover, the aminolysis of D-glycero-D-gulo-heptono-1,4-lactone 1 with o-phenylenediamine 2 was explored using different methodologies. Results indicated that focused ultrasound selectively yielded the amide 3. Studies demonstrated that intensive cavitation can exceed the activation energy without disrupting the thermodynamic equilibrium. Thus, the kinetic product (amide 3) was favored over the thermodynamic product (benzimidazole 4). In contrast, the ultrasonic cleaner led to an incomplete and unselective reaction. On the other hand, thermal induction favored the synthesis of benzimidazole 4, while the mechanochemical synthesis was inefficient in promoting the aminolysis of the γ-lactone 1 with compound 2.

Magnetic Resonance in ChemistryVol. 64(4)
Universidad Autónoma del Estado de Hidalgo (MX), Universidad Autónoma del Estado de Morelos (MX)
Openalex Percentile: Top 94%
Ultrasound and Cavitation Phenomena
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NMR Study of the Aminolysis of D‐Glycero‐D‐gulo‐heptono‐1,4‐lactone With <i>o</i> ‐Phenylenediamine Using Four Synthetic Methodologies — Eltonh Islas‐Trejo, Margarita Tlahuextl, et al. · Magnetic Resonance in Chemistry (2026) | TGRS Research Map | TGRS