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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; in revised form: 28 January 2005 / Accepted: 28 January 2005 / Published: 31 January 2005
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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
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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.

AMA Style

Raczyńska ED, Makowski M, Górnicka E, Darowska M. Ab Initio Studies on the Preferred Site of Protonation in Cytisine in the Gas Phase and Water. International Journal of Molecular Sciences. 2005; 6(1):143-156.

Chicago/Turabian Style

Raczyńska, Ewa D.; Makowski, Mariusz; Górnicka, Elżbieta; Darowska, Małgorzata. 2005. "Ab Initio Studies on the Preferred Site of Protonation in Cytisine in the Gas Phase and Water." Int. J. Mol. Sci. 6, no. 1: 143-156.



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