Carbon acidity of the a-pyridinium carbon of a pyridoxamine analog

Juan Crugeiras; Ana Rios; Tina L. Amyes; John P. Richard

doi:10.1039/b504399a

Carbon acidity of the a-pyridinium carbon of a pyridoxamine analog

Juan Crugeiras
, Ana Rios
, Tina L. Amyes
, John P. Richard

Chemistry

University of Santiago de Compostela

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

16 Scopus citations

Abstract

We report second-order rate constants of K_DO = 120 dm ³ mol^-1 S^-1 and k^B= 6.4 × 10⁴ dm³ mol^-1 S^-1 for exchange for deuterium of the first a-methylene proton of the 4-(aminomethyl)pyridine dication in D₂O at 25 °C and I = 1.0 (KCl). These data are consistent with a carbon acid pK_a between 17 and 19 for ionization of this simple carbon acid and they show that the effect of an α-pyridinium substituent on carbon acidity is similar to that of an α-ester substituent.

Original language	English
Pages (from-to)	2145-2149
Number of pages	5
Journal	Organic and Biomolecular Chemistry
Volume	3
Issue number	11
DOIs	https://doi.org/10.1039/b504399a
State	Published - Jun 7 2005

Access to Document

10.1039/b504399a

Cite this

@article{a28d6c0ed5f347b892e8a38390372610,

title = "Carbon acidity of the a-pyridinium carbon of a pyridoxamine analog",

abstract = "We report second-order rate constants of KDO = 120 dm 3 mol-1 S-1 and kB= 6.4 × 104 dm3 mol-1 S-1 for exchange for deuterium of the first a-methylene proton of the 4-(aminomethyl)pyridine dication in D2O at 25 °C and I = 1.0 (KCl). These data are consistent with a carbon acid pKa between 17 and 19 for ionization of this simple carbon acid and they show that the effect of an α-pyridinium substituent on carbon acidity is similar to that of an α-ester substituent.",

author = "Juan Crugeiras and Ana Rios and Amyes, \{Tina L.\} and Richard, \{John P.\}",

year = "2005",

month = jun,

day = "7",

doi = "10.1039/b504399a",

language = "English",

volume = "3",

pages = "2145--2149",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "11",

}

TY - JOUR

T1 - Carbon acidity of the a-pyridinium carbon of a pyridoxamine analog

AU - Crugeiras, Juan

AU - Rios, Ana

AU - Amyes, Tina L.

AU - Richard, John P.

PY - 2005/6/7

Y1 - 2005/6/7

N2 - We report second-order rate constants of KDO = 120 dm 3 mol-1 S-1 and kB= 6.4 × 104 dm3 mol-1 S-1 for exchange for deuterium of the first a-methylene proton of the 4-(aminomethyl)pyridine dication in D2O at 25 °C and I = 1.0 (KCl). These data are consistent with a carbon acid pKa between 17 and 19 for ionization of this simple carbon acid and they show that the effect of an α-pyridinium substituent on carbon acidity is similar to that of an α-ester substituent.

AB - We report second-order rate constants of KDO = 120 dm 3 mol-1 S-1 and kB= 6.4 × 104 dm3 mol-1 S-1 for exchange for deuterium of the first a-methylene proton of the 4-(aminomethyl)pyridine dication in D2O at 25 °C and I = 1.0 (KCl). These data are consistent with a carbon acid pKa between 17 and 19 for ionization of this simple carbon acid and they show that the effect of an α-pyridinium substituent on carbon acidity is similar to that of an α-ester substituent.

UR - https://www.scopus.com/pages/publications/20844454046

U2 - 10.1039/b504399a

DO - 10.1039/b504399a

M3 - Article

C2 - 15917903

AN - SCOPUS:20844454046

SN - 1477-0520

VL - 3

SP - 2145

EP - 2149

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 11

ER -

Carbon acidity of the a-pyridinium carbon of a pyridoxamine analog

Abstract

Access to Document

Other files and links

Fingerprint

Cite this