A DFT study of the substituent induced shifts of a 5α-OH on ring A                         13                        C chemical shifts of spirostanic sapogenins

Reynier Suardiaz; Javier Pérez; Daniel García; Carlos S. Pérez

doi:10.1016/j.theochem.2006.04.027

A DFT study of the substituent induced shifts of a 5α-OH on ring A ¹³ C chemical shifts of spirostanic sapogenins

Reynier Suardiaz, Javier Pérez, Daniel García, Carlos S. Pérez^*

^*Corresponding author for this work

University of Havana

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

Abstract

The substituent induced shifts (SIS) of a hydroxyl group at position 5α over the ¹³ C chemical shifts on the A ring for some sapogenins have been calculated at B3LYP level of theory with the 6-31G** basis set within the DFT methodology with the GIAO approach. The calculated SIS at beta and gamma carbons fairly agrees with the experimental ones. The experimental anomalous deshielding SIS on several gamma carbons is well reproduced by the calculations and could be related to intramolecular hydrogen bonding.

Original language	English
Pages (from-to)	87-89
Number of pages	3
Journal	Journal of Molecular Structure: THEOCHEM
Volume	769
Issue number	1-3
DOIs	https://doi.org/10.1016/j.theochem.2006.04.027
Publication status	Published - 14 Sept 2006

Keywords

C NMR
DFT
GIAO
SIS
Steroids

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10.1016/j.theochem.2006.04.027

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title = "A DFT study of the substituent induced shifts of a 5α-OH on ring A 13 C chemical shifts of spirostanic sapogenins",

abstract = " The substituent induced shifts (SIS) of a hydroxyl group at position 5α over the 13 C chemical shifts on the A ring for some sapogenins have been calculated at B3LYP level of theory with the 6-31G** basis set within the DFT methodology with the GIAO approach. The calculated SIS at beta and gamma carbons fairly agrees with the experimental ones. The experimental anomalous deshielding SIS on several gamma carbons is well reproduced by the calculations and could be related to intramolecular hydrogen bonding.",

keywords = "C NMR, DFT, GIAO, SIS, Steroids",

author = "Reynier Suardiaz and Javier P{\'e}rez and Daniel Garc{\'i}a and P{\'e}rez, {Carlos S.}",

year = "2006",

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doi = "10.1016/j.theochem.2006.04.027",

language = "English",

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journal = "Journal of Molecular Structure: THEOCHEM",

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A DFT study of the substituent induced shifts of a 5α-OH on ring A ¹³ C chemical shifts of spirostanic sapogenins. / Suardiaz, Reynier; Pérez, Javier; García, Daniel et al.
In: Journal of Molecular Structure: THEOCHEM, Vol. 769, No. 1-3, 14.09.2006, p. 87-89.

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

TY - JOUR

T1 - A DFT study of the substituent induced shifts of a 5α-OH on ring A 13 C chemical shifts of spirostanic sapogenins

AU - Suardiaz, Reynier

AU - Pérez, Javier

AU - García, Daniel

AU - Pérez, Carlos S.

PY - 2006/9/14

Y1 - 2006/9/14

N2 - The substituent induced shifts (SIS) of a hydroxyl group at position 5α over the 13 C chemical shifts on the A ring for some sapogenins have been calculated at B3LYP level of theory with the 6-31G** basis set within the DFT methodology with the GIAO approach. The calculated SIS at beta and gamma carbons fairly agrees with the experimental ones. The experimental anomalous deshielding SIS on several gamma carbons is well reproduced by the calculations and could be related to intramolecular hydrogen bonding.

AB - The substituent induced shifts (SIS) of a hydroxyl group at position 5α over the 13 C chemical shifts on the A ring for some sapogenins have been calculated at B3LYP level of theory with the 6-31G** basis set within the DFT methodology with the GIAO approach. The calculated SIS at beta and gamma carbons fairly agrees with the experimental ones. The experimental anomalous deshielding SIS on several gamma carbons is well reproduced by the calculations and could be related to intramolecular hydrogen bonding.

KW - C NMR

KW - DFT

KW - GIAO

KW - SIS

KW - Steroids

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U2 - 10.1016/j.theochem.2006.04.027

DO - 10.1016/j.theochem.2006.04.027

M3 - Article

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SN - 0166-1280

VL - 769

SP - 87

EP - 89

JO - Journal of Molecular Structure: THEOCHEM

JF - Journal of Molecular Structure: THEOCHEM

IS - 1-3

ER -

A DFT study of the substituent induced shifts of a 5α-OH on ring A 13 C chemical shifts of spirostanic sapogenins

Abstract

Keywords

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A DFT study of the substituent induced shifts of a 5α-OH on ring A ¹³ C chemical shifts of spirostanic sapogenins