Deuterium isotope effects on 13C chemical shifts of negatively charged NH.N systems

Poul Erik Hansen, Mariusz Pietrzak, Eugeniusz Grech, J. Nowicka-Scheibe

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

Resumé

Deuterium isotope effects on 13C chemical shifts are investigated in anions of 1,8-bis(4-toluenesulphonamido)naphthalenes together with N,N-(naphthalene-1,8-diyl)bis(2,2,2-trifluoracetamide) all with bis(1,8-dimethylamino)napthaleneH+ as counter ion. These compounds represent both “static” and equilibrium cases. NMR assignments of the former have been revised. The NH proton is deuteriated. The isotope effects on 13C chemical shifts are rather unusual in these strongly hydrogen bonded systems between a NH and a negatively charged nitrogen atom. 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, 1H and 13C NMR chemical shifts and changes in nuclear shieldings upon deuteriation are calculated using density functional theory methods
OriginalsprogEngelsk
TidsskriftMagnetic Resonance in Chemistry
Vol/bind51
Udgave nummer11
Sider (fra-til)683-689
Antal sider7
ISSN0749-1581
DOI
StatusUdgivet - 2013

Emneord

  • Isotope effects
  • NMR
  • Hydrogen bonding

Citer dette

Hansen, Poul Erik ; Pietrzak, Mariusz ; Grech, Eugeniusz ; Nowicka-Scheibe, J. / Deuterium isotope effects on 13C chemical shifts of negatively charged NH.N systems. I: Magnetic Resonance in Chemistry. 2013 ; Bind 51, Nr. 11. s. 683-689.
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title = "Deuterium isotope effects on 13C chemical shifts of negatively charged NH.N systems",
abstract = "Deuterium isotope effects on 13C chemical shifts are investigated in anions of 1,8-bis(4-toluenesulphonamido)naphthalenes together with N,N-(naphthalene-1,8-diyl)bis(2,2,2-trifluoracetamide) all with bis(1,8-dimethylamino)napthaleneH+ as counter ion. These compounds represent both “static” and equilibrium cases. NMR assignments of the former have been revised. The NH proton is deuteriated. The isotope effects on 13C chemical shifts are rather unusual in these strongly hydrogen bonded systems between a NH and a negatively charged nitrogen atom. 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, 1H and 13C NMR chemical shifts and changes in nuclear shieldings upon deuteriation are calculated using density functional theory methods",
keywords = "Isotope effects, NMR, Hydrogen bonding, Isotope effects, NMR, Hydrogen bonding",
author = "Hansen, {Poul Erik} and Mariusz Pietrzak and Eugeniusz Grech and J. Nowicka-Scheibe",
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doi = "10.1002/mrc.4000",
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Deuterium isotope effects on 13C chemical shifts of negatively charged NH.N systems. / Hansen, Poul Erik; Pietrzak, Mariusz; Grech, Eugeniusz; Nowicka-Scheibe, J.

I: Magnetic Resonance in Chemistry, Bind 51, Nr. 11, 2013, s. 683-689.

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

TY - JOUR

T1 - Deuterium isotope effects on 13C chemical shifts of negatively charged NH.N systems

AU - Hansen, Poul Erik

AU - Pietrzak, Mariusz

AU - Grech, Eugeniusz

AU - Nowicka-Scheibe, J.

PY - 2013

Y1 - 2013

N2 - Deuterium isotope effects on 13C chemical shifts are investigated in anions of 1,8-bis(4-toluenesulphonamido)naphthalenes together with N,N-(naphthalene-1,8-diyl)bis(2,2,2-trifluoracetamide) all with bis(1,8-dimethylamino)napthaleneH+ as counter ion. These compounds represent both “static” and equilibrium cases. NMR assignments of the former have been revised. The NH proton is deuteriated. The isotope effects on 13C chemical shifts are rather unusual in these strongly hydrogen bonded systems between a NH and a negatively charged nitrogen atom. 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, 1H and 13C NMR chemical shifts and changes in nuclear shieldings upon deuteriation are calculated using density functional theory methods

AB - Deuterium isotope effects on 13C chemical shifts are investigated in anions of 1,8-bis(4-toluenesulphonamido)naphthalenes together with N,N-(naphthalene-1,8-diyl)bis(2,2,2-trifluoracetamide) all with bis(1,8-dimethylamino)napthaleneH+ as counter ion. These compounds represent both “static” and equilibrium cases. NMR assignments of the former have been revised. The NH proton is deuteriated. The isotope effects on 13C chemical shifts are rather unusual in these strongly hydrogen bonded systems between a NH and a negatively charged nitrogen atom. 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, 1H and 13C NMR chemical shifts and changes in nuclear shieldings upon deuteriation are calculated using density functional theory methods

KW - Isotope effects

KW - NMR

KW - Hydrogen bonding

KW - Isotope effects

KW - NMR

KW - Hydrogen bonding

U2 - 10.1002/mrc.4000

DO - 10.1002/mrc.4000

M3 - Journal article

VL - 51

SP - 683

EP - 689

JO - Magnetic Resonance in Chemistry

JF - Magnetic Resonance in Chemistry

SN - 0749-1581

IS - 11

ER -