Next Article in Journal
Ab initio post-HF CCSD(T) Calculations for Triplet and Singlet Methylene in Four consecutive Dunning Basis Sets with Extrapolations to Infinite Limits for Various Molecular Properties
Previous Article in Journal
Reduction of Sulfur Dioxide on Carbons Catalyzed by Salts
Int. J. Mol. Sci. 2005, 6(1), 143-156; doi:10.3390/i6010143
Article

Ab Initio Studies on the Preferred Site of Protonation in Cytisine in the Gas Phase and Water

1,* , 2, 3 and 3
Received: 24 June 2004 / Revised: 28 January 2005 / Accepted: 28 January 2005 / Published: 31 January 2005
Download PDF [237 KB, uploaded 19 June 2014]

Abstract

Ab initio calculations (HF, MP2, DFT for isolated and PCM for solvated molecules) were performed for cytisine (1) and its model compounds: N-methyl-2-pyridone (2) and piperidine (3). Among three heteroatomic functions (carbonyl oxygen, pyridone and piperidine nitrogens) considered as the possible sites of protonation in 1, surprisingly the carbonyl oxygen takes preferentially the proton in the gas phase whereas in water the piperidine nitrogen is firstly protonated. For model compounds, the piperidine nitrogen in 3 is more basic than the carbonyl oxygen in 2 in both, the gas phase and water.
Keywords: Cytisine; Site of protonation; Ab initio calculations; PCM; Gas phase and Solution Cytisine; Site of protonation; Ab initio calculations; PCM; Gas phase and Solution
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Share & Cite This Article

Further Mendeley | CiteULike
Export to BibTeX |
EndNote
MDPI and ACS Style

Raczyńska, E.D.; Makowski, M.; Górnicka, E.; Darowska, M. Ab Initio Studies on the Preferred Site of Protonation in Cytisine in the Gas Phase and Water. Int. J. Mol. Sci. 2005, 6, 143-156.

View more citation formats

Related Articles

Article Metrics

For more information on the journal, click here

Comments

Cited By

[Return to top]
Int. J. Mol. Sci. EISSN 1422-0067 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert