Deuterium isotope effects on 13C chemical shifts of 10-Hydroxybenzo[h]quinolines

Poul Erik Hansen, Fadhil S. Kamounah, Daniel T. Gryko

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

Resumé

Deuterium isotope effects on 13C-NMR chemical shifts are investigated in a series of 10-hydroxybenzo[h]quinolines (HBQ’s) The OH proton is deuteriated. The isotope effects on 13C chemical shifts in these hydrogen bonded systems are rather unusual. The formal four-bond effects are found to be negative, indicating transmission via the hydrogen bond. In addition unusual long-range effects are seen. Structures, NMR chemical shifts and changes in nuclear shieldings upon deuteriation are calculated using DFT methods. Two-bond deuterium isotope effects on 13C chemical shifts are correlated with calculated OH stretching frequencies. Isotope effects on chemical shifts are calculated for systems with OH exchanged by OD. Hydrogen bond potentials are discussed. New and more soluble nitro derivatives are synthesized.
OriginalsprogEngelsk
TidsskriftMolecules
Vol/bind18
Udgave nummer4
Sider (fra-til)4544-4560
Antal sider16
ISSN1420-3049
DOI
StatusUdgivet - 2013

Emneord

  • Isotope effects
  • hydroxybenzoquinolines
  • hydrogen bonding
  • DFT calculations

Citer dette

Hansen, Poul Erik ; Kamounah, Fadhil S. ; Gryko, Daniel T. / Deuterium isotope effects on 13C chemical shifts of 10-Hydroxybenzo[h]quinolines. I: Molecules. 2013 ; Bind 18, Nr. 4. s. 4544-4560.
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title = "Deuterium isotope effects on 13C chemical shifts of 10-Hydroxybenzo[h]quinolines",
abstract = "Deuterium isotope effects on 13C-NMR chemical shifts are investigated in a series of 10-hydroxybenzo[h]quinolines (HBQ’s) The OH proton is deuteriated. The isotope effects on 13C chemical shifts in these hydrogen bonded systems are rather unusual. The formal four-bond effects are found to be negative, indicating transmission via the hydrogen bond. In addition unusual long-range effects are seen. Structures, NMR chemical shifts and changes in nuclear shieldings upon deuteriation are calculated using DFT methods. Two-bond deuterium isotope effects on 13C chemical shifts are correlated with calculated OH stretching frequencies. Isotope effects on chemical shifts are calculated for systems with OH exchanged by OD. Hydrogen bond potentials are discussed. New and more soluble nitro derivatives are synthesized.",
keywords = "Isotope effects, hydroxybenzoquinolines, hydrogen bonding, DFT calculations, Isotope effects, hydroxybenzoquinolines, hydrogen bonding, DFT calculations",
author = "Hansen, {Poul Erik} and Kamounah, {Fadhil S.} and Gryko, {Daniel T.}",
year = "2013",
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Deuterium isotope effects on 13C chemical shifts of 10-Hydroxybenzo[h]quinolines. / Hansen, Poul Erik; Kamounah, Fadhil S.; Gryko, Daniel T.

I: Molecules, Bind 18, Nr. 4, 2013, s. 4544-4560.

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

TY - JOUR

T1 - Deuterium isotope effects on 13C chemical shifts of 10-Hydroxybenzo[h]quinolines

AU - Hansen, Poul Erik

AU - Kamounah, Fadhil S.

AU - Gryko, Daniel T.

PY - 2013

Y1 - 2013

N2 - Deuterium isotope effects on 13C-NMR chemical shifts are investigated in a series of 10-hydroxybenzo[h]quinolines (HBQ’s) The OH proton is deuteriated. The isotope effects on 13C chemical shifts in these hydrogen bonded systems are rather unusual. The formal four-bond effects are found to be negative, indicating transmission via the hydrogen bond. In addition unusual long-range effects are seen. Structures, NMR chemical shifts and changes in nuclear shieldings upon deuteriation are calculated using DFT methods. Two-bond deuterium isotope effects on 13C chemical shifts are correlated with calculated OH stretching frequencies. Isotope effects on chemical shifts are calculated for systems with OH exchanged by OD. Hydrogen bond potentials are discussed. New and more soluble nitro derivatives are synthesized.

AB - Deuterium isotope effects on 13C-NMR chemical shifts are investigated in a series of 10-hydroxybenzo[h]quinolines (HBQ’s) The OH proton is deuteriated. The isotope effects on 13C chemical shifts in these hydrogen bonded systems are rather unusual. The formal four-bond effects are found to be negative, indicating transmission via the hydrogen bond. In addition unusual long-range effects are seen. Structures, NMR chemical shifts and changes in nuclear shieldings upon deuteriation are calculated using DFT methods. Two-bond deuterium isotope effects on 13C chemical shifts are correlated with calculated OH stretching frequencies. Isotope effects on chemical shifts are calculated for systems with OH exchanged by OD. Hydrogen bond potentials are discussed. New and more soluble nitro derivatives are synthesized.

KW - Isotope effects

KW - hydroxybenzoquinolines

KW - hydrogen bonding

KW - DFT calculations

KW - Isotope effects

KW - hydroxybenzoquinolines

KW - hydrogen bonding

KW - DFT calculations

U2 - 10.3390/molecules18044544

DO - 10.3390/molecules18044544

M3 - Journal article

VL - 18

SP - 4544

EP - 4560

JO - Molecules

JF - Molecules

SN - 1420-3049

IS - 4

ER -