Synthesis, molecular structure, conformational, and intramolecular hydrogen bond strength of ethyl 3-amino-2-butenoate and its N-Me, N-Ph, and N-Bn analogs; An experimental and theoretical study

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Standard

Synthesis, molecular structure, conformational, and intramolecular hydrogen bond strength of ethyl 3-amino-2-butenoate and its N-Me, N-Ph, and N-Bn analogs; An experimental and theoretical study. / Bazrafshan, Mahmoud; Vakili, Mohammad; Tayyari, Sayyed Faramarz; Kamounah, Fadhil S.; Hansen, Poul Erik; Shiri, Ali.

I: Journal of Molecular Structure, Bind 1274, Nr. Part 2, 134479, 2023.

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt

Harvard

Bazrafshan, M, Vakili, M, Tayyari, SF, Kamounah, FS, Hansen, PE & Shiri, A 2023, 'Synthesis, molecular structure, conformational, and intramolecular hydrogen bond strength of ethyl 3-amino-2-butenoate and its N-Me, N-Ph, and N-Bn analogs; An experimental and theoretical study', Journal of Molecular Structure, bind 1274, nr. Part 2, 134479. https://doi.org/10.1016/j.molstruc.2022.134479

APA

Bazrafshan, M., Vakili, M., Tayyari, S. F., Kamounah, F. S., Hansen, P. E., & Shiri, A. (2023). Synthesis, molecular structure, conformational, and intramolecular hydrogen bond strength of ethyl 3-amino-2-butenoate and its N-Me, N-Ph, and N-Bn analogs; An experimental and theoretical study. Journal of Molecular Structure, 1274(Part 2), [134479]. https://doi.org/10.1016/j.molstruc.2022.134479

Vancouver

Bazrafshan M, Vakili M, Tayyari SF, Kamounah FS, Hansen PE, Shiri A. Synthesis, molecular structure, conformational, and intramolecular hydrogen bond strength of ethyl 3-amino-2-butenoate and its N-Me, N-Ph, and N-Bn analogs; An experimental and theoretical study. Journal of Molecular Structure. 2023;1274(Part 2). 134479. https://doi.org/10.1016/j.molstruc.2022.134479

Author

Bazrafshan, Mahmoud ; Vakili, Mohammad ; Tayyari, Sayyed Faramarz ; Kamounah, Fadhil S. ; Hansen, Poul Erik ; Shiri, Ali. / Synthesis, molecular structure, conformational, and intramolecular hydrogen bond strength of ethyl 3-amino-2-butenoate and its N-Me, N-Ph, and N-Bn analogs; An experimental and theoretical study. I: Journal of Molecular Structure. 2023 ; Bind 1274, Nr. Part 2.

Bibtex

@article{c443d14312be4dc9968686e669676a5c,
title = "Synthesis, molecular structure, conformational, and intramolecular hydrogen bond strength of ethyl 3-amino-2-butenoate and its N-Me, N-Ph, and N-Bn analogs; An experimental and theoretical study",
abstract = "Amino derivatives of ethyl acetoacetate like ethyl (Z)- 3-(amino)but-2-enoate (EAB), ethyl (Z)- 3-(methylamino)but-2-enoate (Me-EAB), ethyl (Z)- 3-(phenylamino)but-2-enoate (Ph-EAB), and ethyl (Z)- 3-(benzylamino)but-2-enoate (Bn-EAB) were synthesized. Their structures, conformations, and intramolecular hydrogen bonding (IHB) is characterized using computational analysis (density functional theory, DFT, methods) at the B3LYP/6-311++G(d,p) level and spectroscopic techniques)IR, UV, and NMR). All the mentioned theoretical and experimental results were compared to those of (Z)-methyl 3-aminobut-2-enoate (MAB). The vibrational spectra of EAB are fully assigned. Vibrational spectroscopy results confirmed the existence of two conformers of title molecules. DFT calculations at the B3LYP/6-311++G(d,p) level show the calculated Nsingle bondH bond lengths in EAB, Me-EAB, Ph-EAB, Bn-EAB, and MAB are 1.015, 1.017, 1.022, 1.018, and 1.014 Ǻ, respectively. Also, according to the natural bond orbital (NBO) results, the σN-H10↔LP(2)O7 interactions for EAB, Me-EAB, Ph-EAB, Bn-EAB, and MAB are 5.21, 6.77, 8.65, 7.18, and 5.11 kcal/mol, respectively. So, the trend in IHB strength is: Ph-EAB > Bn-EAB ∼ Me-EAB > EAB ∼ MAB, which also agrees with the mentioned experimental results. The mentioned trend also is confirmed by the LP(O7)↔σNsingle bondH steric exchange interaction.",
keywords = "Intramolecular hydrogen bond, NMR, Vibrational spectroscopy, DFT, Ethyl(Z)-3-(amino)but-2-enoate",
author = "Mahmoud Bazrafshan and Mohammad Vakili and Tayyari, {Sayyed Faramarz} and Kamounah, {Fadhil S.} and Hansen, {Poul Erik} and Ali Shiri",
year = "2023",
doi = "10.1016/j.molstruc.2022.134479",
language = "English",
volume = "1274",
journal = "Journal of Molecular Structure",
issn = "0022-2860",
publisher = "Elsevier",
number = "Part 2",

}

RIS

TY - JOUR

T1 - Synthesis, molecular structure, conformational, and intramolecular hydrogen bond strength of ethyl 3-amino-2-butenoate and its N-Me, N-Ph, and N-Bn analogs; An experimental and theoretical study

AU - Bazrafshan, Mahmoud

AU - Vakili, Mohammad

AU - Tayyari, Sayyed Faramarz

AU - Kamounah, Fadhil S.

AU - Hansen, Poul Erik

AU - Shiri, Ali

PY - 2023

Y1 - 2023

N2 - Amino derivatives of ethyl acetoacetate like ethyl (Z)- 3-(amino)but-2-enoate (EAB), ethyl (Z)- 3-(methylamino)but-2-enoate (Me-EAB), ethyl (Z)- 3-(phenylamino)but-2-enoate (Ph-EAB), and ethyl (Z)- 3-(benzylamino)but-2-enoate (Bn-EAB) were synthesized. Their structures, conformations, and intramolecular hydrogen bonding (IHB) is characterized using computational analysis (density functional theory, DFT, methods) at the B3LYP/6-311++G(d,p) level and spectroscopic techniques)IR, UV, and NMR). All the mentioned theoretical and experimental results were compared to those of (Z)-methyl 3-aminobut-2-enoate (MAB). The vibrational spectra of EAB are fully assigned. Vibrational spectroscopy results confirmed the existence of two conformers of title molecules. DFT calculations at the B3LYP/6-311++G(d,p) level show the calculated Nsingle bondH bond lengths in EAB, Me-EAB, Ph-EAB, Bn-EAB, and MAB are 1.015, 1.017, 1.022, 1.018, and 1.014 Ǻ, respectively. Also, according to the natural bond orbital (NBO) results, the σN-H10↔LP(2)O7 interactions for EAB, Me-EAB, Ph-EAB, Bn-EAB, and MAB are 5.21, 6.77, 8.65, 7.18, and 5.11 kcal/mol, respectively. So, the trend in IHB strength is: Ph-EAB > Bn-EAB ∼ Me-EAB > EAB ∼ MAB, which also agrees with the mentioned experimental results. The mentioned trend also is confirmed by the LP(O7)↔σNsingle bondH steric exchange interaction.

AB - Amino derivatives of ethyl acetoacetate like ethyl (Z)- 3-(amino)but-2-enoate (EAB), ethyl (Z)- 3-(methylamino)but-2-enoate (Me-EAB), ethyl (Z)- 3-(phenylamino)but-2-enoate (Ph-EAB), and ethyl (Z)- 3-(benzylamino)but-2-enoate (Bn-EAB) were synthesized. Their structures, conformations, and intramolecular hydrogen bonding (IHB) is characterized using computational analysis (density functional theory, DFT, methods) at the B3LYP/6-311++G(d,p) level and spectroscopic techniques)IR, UV, and NMR). All the mentioned theoretical and experimental results were compared to those of (Z)-methyl 3-aminobut-2-enoate (MAB). The vibrational spectra of EAB are fully assigned. Vibrational spectroscopy results confirmed the existence of two conformers of title molecules. DFT calculations at the B3LYP/6-311++G(d,p) level show the calculated Nsingle bondH bond lengths in EAB, Me-EAB, Ph-EAB, Bn-EAB, and MAB are 1.015, 1.017, 1.022, 1.018, and 1.014 Ǻ, respectively. Also, according to the natural bond orbital (NBO) results, the σN-H10↔LP(2)O7 interactions for EAB, Me-EAB, Ph-EAB, Bn-EAB, and MAB are 5.21, 6.77, 8.65, 7.18, and 5.11 kcal/mol, respectively. So, the trend in IHB strength is: Ph-EAB > Bn-EAB ∼ Me-EAB > EAB ∼ MAB, which also agrees with the mentioned experimental results. The mentioned trend also is confirmed by the LP(O7)↔σNsingle bondH steric exchange interaction.

KW - Intramolecular hydrogen bond

KW - NMR

KW - Vibrational spectroscopy

KW - DFT

KW - Ethyl(Z)-3-(amino)but-2-enoate

U2 - 10.1016/j.molstruc.2022.134479

DO - 10.1016/j.molstruc.2022.134479

M3 - Journal article

VL - 1274

JO - Journal of Molecular Structure

JF - Journal of Molecular Structure

SN - 0022-2860

IS - Part 2

M1 - 134479

ER -

ID: 339632958