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International Journal of Pharmaceutics

Volumn 448, Issue 1, 2013, Pages 123-131

Quantification of protonation in organic solvents using solution NMR spectroscopy: Implication in salt formation

(3) Kim, Hyungchul a,b Babu, Charles R c Burgess, Diane J b

a ASTRAZENECA (United Kingdom)

b UNIVERSITY OF CONNECTICUT (United States)

c NOVARTIS INSTITUTES FOR BIOMEDICAL RESEARCH (United States)

Author keywords

Chemical shift changes; Counterion; NMR; Protonation pKa; Salt formation; Solvent effect

Indexed keywords

DIMETHYL SULFOXIDE; METHANOL; ORGANIC SOLVENT; WATER;

ARTICLE; CONTROLLED STUDY; IONIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; QUANTITATIVE ANALYSIS; TITRIMETRY;

DIMETHYL SULFOXIDE; ETHYLENEDIAMINES; HETEROCYCLIC COMPOUNDS, 1-RING; MAGNETIC RESONANCE SPECTROSCOPY; METHANOL; PROTONS; QUINUCLIDINES; SALTS; SOLUTIONS; SOLVENTS; WATER;

EID: 84875949843 PISSN: 03785173 EISSN: 18733476 Source Type: Journal
DOI: 10.1016/j.ijpharm.2013.03.040 Document Type: Article

Times cited : (9)

References (25)

1
- 0027508841
- PH-Metric log P. 3. Glass electrode calibration in methanol-water, applied to pK(a) determination of water-insoluble substances
- DOI 10.1021/ac00049a010
- a determination of water-insoluble substances Anal. Chem. 65 1993 42 49 (Pubitemid 23037525)
- (1993) Analytical Chemistry , vol.65 , Issue.1 , pp. 42-49
- Avdeef, A.¹ Comer, J.E.A.² Thomson, S.J.³

2
- 0032585804
- PH-metric logP 11. pK(a) determination of water-insoluble drugs in organic solvent-water mixtures
- DOI 10.1016/S0731-7085(98)00235-0, PII S0731708598002350
- a determination of water-insoluble drugs in organic solvent-water mixtures J. Pharm. Biomed. Anal. 20 1999 631 641 (Pubitemid 29245964)
- (1999) Journal of Pharmaceutical and Biomedical Analysis , vol.20 , Issue.4 , pp. 631-641
- Avdeef, A.¹ Box, K.J.² Comer, J.E.A.³ Gilges, M.⁴ Hadley, M.⁵ Hibbert, C.⁶ Patterson, W.⁷ Tam, K.Y.⁸

3
- 0032938611
- Chromatographic behaviour of ionizable compounds in liquid chromatography. Part 1. pH scale, pK(a) and pH(S) values for standard buffers in tetrahydrofuran-water
- DOI 10.1016/S0003-2670(99)00133-6, PII S0003267099001336
- a and pHS values for standard buffers in tetrahydrofuran-water Anal. Chim. Acta 389 1999 31 42 (Pubitemid 29236092)
- (1999) Analytica Chimica Acta , vol.389 , Issue.1-3 , pp. 31-42
- Barbosa, J.¹ Barron, D.² Buti, S.³

4
- 0034345216
- Salt selection and optimization procedures for pharmaceutical new chemical entities
- R.J. Bastin, M.J. Bowker, and B.J. Slater Salt selection and optimization procedures for pharmaceutical new chemical entities Org. Process Res. Dev. 4 2000 427 435
- (2000) Org. Process Res. Dev. , vol.4 , pp. 427-435
- Bastin, R.J.¹ Bowker, M.J.² Slater, B.J.³

5
- 34249088975
- Structure, solubility, screening, and synthesis of molecular salts
- DOI 10.1002/jps.20927
- S.N. Black, E.A. Collier, R.J. Davey, and R.J. Roberts Structure, solubility, screening, and synthesis of molecular salts J. Pharm. Sci. 96 2007 1053 1068 (Pubitemid 46797476)
- (2007) Journal of Pharmaceutical Sciences , vol.96 , Issue.5 , pp. 1053-1068
- Black, S.N.¹ Collier, E.A.² Davey, R.J.³ Roberts, R.J.⁴

6
- 0018412446
- Solubility of doxycycline in aqueous solution
- Joseph B. Bogardus, and Robert K. Blackwood Jr. Solubility of doxycycline in aqueous solution J. Pharm. Sci. 68 1979 188 194 (Pubitemid 9117123)
- (1979) Journal of Pharmaceutical Sciences , vol.68 , Issue.2 , pp. 188-194
- Bogardus, J.B.¹ Blackwood Jr., R.K.²

7
- 0344887064
- Equilibrium acidities in dimethyl sulfoxide solution
- F.G. Bordwell Equilibrium acidities in dimethyl sulfoxide solution Acc. Chem. Res. 21 1988 456 463
- (1988) Acc. Chem. Res. , vol.21 , pp. 456-463
- Bordwell, F.G.¹

8
- 84876666795
- a Table (Acidity in DMSO)
- a Table (Acidity in DMSO), http://www.chem.wisc. edu/areas/reich/pkatable/index.htm.

9
- 0346458663
- Mechanochemical preparation of hydrogen-bonded adducts between the diamine 1,4-diazabicyclo[2.2.2]octane and dicarboxylic acids of variable chain length: An X-ray diffraction and solid-state NMR study
- D. Braga, L. Maini, G. de Sanctis, K. Rubini, F. Grepioni, M.R. Chierotti, and R. Gobetto Mechanochemical preparation of hydrogen-bonded adducts between the diamine 1,4-diazabicyclo[2.2.2]octane and dicarboxylic acids of variable chain length: an X-ray diffraction and solid-state NMR study Chem. Eur. J. 9 2003 5538 5548
- (2003) Chem. Eur. J. , vol.9 , pp. 5538-5548
- Braga, D.¹ Maini, L.² De Sanctis, G.³ Rubini, K.⁴ Grepioni, F.⁵ Chierotti, M.R.⁶ Gobetto, R.⁷

10
- 34250791543
- The salt-cocrystal continuum: The influence of crystal structure on ionization state
- DOI 10.1021/mp0601345
- Scott L. Childs, G. Patrick Stahly, and A. Park The salt-cocrystal continuum: the influence of crystal structure on ionization state Mol. Pharm. 4 2007 323 338 (Pubitemid 46983949)
- (2007) Molecular Pharmaceutics , vol.4 , Issue.3 , pp. 323-338
- Childs, S.L.¹ Stahly, G.P.² Park, A.³

11
- 84867907561
- 90th ed.; David R. Lide, ISBN-13:9781420090840
- CRC Handbook of Chemistry and Physics. 90th ed.; David R. Lide, ISBN-13:9781420090840. pp. 8-48.
- CRC Handbook of Chemistry and Physics , pp. 8-48

12
- 52649162859
- Synthesis of stable cysteine-heterodisulphides
- DOI 10.1023/A:1021312807664
- E. Cros, M. Planas, and E. Bardaji Synthesis of stable cysteine-heterodisulphides Lett. Pept. Sci. 9 2002 1 4 (Pubitemid 36082957)
- (2002) Letters in Peptide Science , vol.9 , Issue.1 , pp. 1-4
- Cros, E.¹ Planas, M.² Bardaji, E.³

13
- 0036806990
- Studies on the macroscopic protonation constants of some α-amino acids in ethanol-water mixtures
- DOI 10.1016/S0003-2697(02)00254-3, PII S0003269702002543
- A. Dogan, F. Köseoglu, and E. KilIç Studies on the macroscopic protonation constants of some [alpha]-amino acids in ethanol-water mixtures Anal. Biochem. 309 2002 75 78 (Pubitemid 35305792)
- (2002) Analytical Biochemistry , vol.309 , Issue.1 , pp. 75-78
- Dogan, A.¹ Koseoglu, F.² Kilic, E.³

14
- 84876685168
- a's of Inorganic and Oxo-Acids, 2012-09-24.
- a's of Inorganic and Oxo-Acids, 2012-09-24 http://evans.harvard.edu/pdf/evans-pKa-table.pdf.

15
- 0031794167
- Dissociation const of neutral and charged acids in methyl alcohol
- Fernando Dissociation const of neutral and charged acids in methyl alcohol Aanl. Chim. Acta 374 1998 309 324
- (1998) Aanl. Chim. Acta , vol.374 , pp. 309-324
- Fernando¹

16
- 34447649709
- Acidity of several polyprotic acids, amiodarone and quetiapine hemifumarate in pure methanol
- DOI 10.1016/j.talanta.2007.03.010, PII S0039914007001865
- G. Garrido, V. de Nogales, C. R'afols, and E. Bosch Acidity of several polyprotic acids, amiodarone and quetiapine hemifumarate in pure methanol Talanta 73 2007 115 120 (Pubitemid 47090225)
- (2007) Talanta , vol.73 , Issue.1 , pp. 115-120
- Garrido, G.¹ De Nogales, V.² Rafols, C.³ Bosch, E.⁴

17
- 0042058435
- Wiley-VCH Zurich
- P. Heinrich Stahl Appendix. Handbook of Pharmaceutical Salts: Properties, Selection, and Use 2002 Wiley-VCH Zurich pp. 329-350
- (2002) Appendix. Handbook of Pharmaceutical Salts: Properties, Selection, and Use , pp. 329-350
- Heinrich Stahl, P.¹

18
- 0001730883
- Ionization const of fluorinated acids
- A.L. Henne, and C.J. Fox Ionization const of fluorinated acids J. Am. Chem. Soc. 73 1953 2323
- (1953) J. Am. Chem. Soc. , vol.73 , pp. 2323
- Henne, A.L.¹ Fox, C.J.²

19
- 0004099201
- Wiley-VCH Weinheim
- K. Izutsu Electrochemistry in Nonaqueous Solutions 2002 Wiley-VCH Weinheim pp. 25-83
- (2002) Electrochemistry in Nonaqueous Solutions , pp. 25-83
- Izutsu, K.¹

20
- 67649649925
- Evaluation of solvent effects on protonation using NMR spectroscopy: Implication in salt formation
- H. Kim, J. Gao, and D.J. Burgess Evaluation of solvent effects on protonation using NMR spectroscopy: implication in salt formation Int. J. Pharm. 377 2009 105 111
- (2009) Int. J. Pharm. , vol.377 , pp. 105-111
- Kim, H.¹ Gao, J.² Burgess, D.J.³

21
- 0344255603
- 2O
- DOI 10.1016/j.jinorgbio.2003.10.001
- 2O J. Inorg. Biochem. 98 2004 161 166 (Pubitemid 37495021)
- (2004) Journal of Inorganic Biochemistry , vol.98 , Issue.1 , pp. 161-166
- Krezel, A.¹ Bal, W.²

22
- 0030176649
- as
- as Anal. Chem. 68 1996 2127 2134
- (1996) Anal. Chem. , vol.68 , pp. 2127-2134
- Perrin, C.L.¹ Fabian, M.A.²

23
- 0032916498
- Ionization constants of weak acids and bases in organic solvents
- DOI 10.1016/S0165-022X(98)00033-5, PII S0165022X98000335
- K. Sarminiand, and E. Kenndler Ionization constants of weak acids and bases in organic solvents J. Biochem. Biophys. Methods 38 1999 123 137 (Pubitemid 29010283)
- (1999) Journal of Biochemical and Biophysical Methods , vol.38 , Issue.2 , pp. 123-137
- Sarmini, K.¹ Kenndler, E.²

24
- 1042284960
- Salt selection strategies
- P.H.S.a.C.G. Wermuth, Wiley-VCH Zurich
- A.T.M. Serajuddin, and M. Pudipeddi Salt selection strategies P.H.S.a.C.G. Wermuth, Handbook of Pharmaceutical Salts: Properties, Selection, and Use 2002 Wiley-VCH Zurich 135 160
- (2002) Handbook of Pharmaceutical Salts: Properties, Selection, and Use , pp. 135-160
- Serajuddin, A.T.M.¹ Pudipeddi, M.²

25
- 0142028495
- Potentiometric pK(a) determination of water-insoluble compounds: Validation study in methanol/water mixtures
- DOI 10.1016/S0378-5173(97)04907-7, PII S0378517397049077
- a determination of water-insoluble compounds: validation study in methanol/water mixtures Int. J. Pharm. 151 1997 235 248 (Pubitemid 27223371)
- (1997) International Journal of Pharmaceutics , vol.151 , Issue.2 , pp. 235-248
- Takacs-Novak, K.¹ Box, K.J.² Avdeef, A.³

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