Tautomerism of amidoximes and other oxime species

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Tautomerism of amidoximes and other oxime species. / Novikov, Alexander S.; Bolotin, Dmitrii S.

In: Journal of Physical Organic Chemistry, Vol. 31, No. 3, e3772, 03.2018.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{53130e63de61472d8e23899b91506827,

title = "Tautomerism of amidoximes and other oxime species",

abstract = "The tautomerism of the aliphatic MeC(NH2)NOH and the aromatic PhC(NH2)NOH amidoximes in protic (H2O, MeOH) and aprotic (Me2CO, Me2SO, and CHCl3) solvents was studied by density functional theory calculations at the M06-2X/6-311+G(d,p) level of theory. In both types of solutions, these species exist in 3 tautomeric forms, viz, (Z)- or (E)-amidoximes, and (Z)-aminonitrone. The (Z)-form is the dominant, and energy gap between the (Z)- and (E)-tautomers of the amidoximes slightly depends on the nature of a solvent and significantly higher than that for other oxime species. For the amidoximes, the zwitterionic (Z)-aminonitrone form is stabilized by protic solvents. The oxime-nitrone energy gap is reduced by electron-donor substituents at the oxime moiety at different types of oxime species.",

keywords = "Amidoximes, Density functional theory calculations, Tautomerism, tautomerism, amidoximes, density functional theory calculations, 1,2,4-OXADIAZOLES, MECHANISM, NITROSOMETHANE, EXCITED-STATES, CHEMISTRY, ADSORBENT, GENERATION",

author = "Novikov, {Alexander S.} and Bolotin, {Dmitrii S.}",

year = "2018",

month = mar,

doi = "10.1002/poc.3772",

language = "English",

volume = "31",

journal = "Journal of Physical Organic Chemistry",

issn = "0894-3230",

publisher = "Wiley-Blackwell",

number = "3",

}

RIS

TY - JOUR

T1 - Tautomerism of amidoximes and other oxime species

AU - Novikov, Alexander S.

AU - Bolotin, Dmitrii S.

PY - 2018/3

Y1 - 2018/3

N2 - The tautomerism of the aliphatic MeC(NH2)NOH and the aromatic PhC(NH2)NOH amidoximes in protic (H2O, MeOH) and aprotic (Me2CO, Me2SO, and CHCl3) solvents was studied by density functional theory calculations at the M06-2X/6-311+G(d,p) level of theory. In both types of solutions, these species exist in 3 tautomeric forms, viz, (Z)- or (E)-amidoximes, and (Z)-aminonitrone. The (Z)-form is the dominant, and energy gap between the (Z)- and (E)-tautomers of the amidoximes slightly depends on the nature of a solvent and significantly higher than that for other oxime species. For the amidoximes, the zwitterionic (Z)-aminonitrone form is stabilized by protic solvents. The oxime-nitrone energy gap is reduced by electron-donor substituents at the oxime moiety at different types of oxime species.

AB - The tautomerism of the aliphatic MeC(NH2)NOH and the aromatic PhC(NH2)NOH amidoximes in protic (H2O, MeOH) and aprotic (Me2CO, Me2SO, and CHCl3) solvents was studied by density functional theory calculations at the M06-2X/6-311+G(d,p) level of theory. In both types of solutions, these species exist in 3 tautomeric forms, viz, (Z)- or (E)-amidoximes, and (Z)-aminonitrone. The (Z)-form is the dominant, and energy gap between the (Z)- and (E)-tautomers of the amidoximes slightly depends on the nature of a solvent and significantly higher than that for other oxime species. For the amidoximes, the zwitterionic (Z)-aminonitrone form is stabilized by protic solvents. The oxime-nitrone energy gap is reduced by electron-donor substituents at the oxime moiety at different types of oxime species.

KW - Amidoximes

KW - Density functional theory calculations

KW - Tautomerism

KW - tautomerism

KW - amidoximes

KW - density functional theory calculations

KW - 1,2,4-OXADIAZOLES

KW - MECHANISM

KW - NITROSOMETHANE

KW - EXCITED-STATES

KW - CHEMISTRY

KW - ADSORBENT

KW - GENERATION

UR - http://www.scopus.com/inward/record.url?scp=85028909781&partnerID=8YFLogxK

UR - http://www.mendeley.com/research/tautomerism-amidoximes-other-oxime-species

U2 - 10.1002/poc.3772

DO - 10.1002/poc.3772

M3 - Article

AN - SCOPUS:85028909781

VL - 31

JO - Journal of Physical Organic Chemistry

JF - Journal of Physical Organic Chemistry

SN - 0894-3230

IS - 3

M1 - e3772

ER -

ID: 9169868