Gas chromatographic study of the hydrogen bonding of aliphatic alcohols to tri-n-octylphosphine oxide.
Retention volumes of 21 aliphatic alcohols were measured at five temperatures between 30 and 60 degrees C in columns packed with different percentages of squalane or with solutions of tri-n-octylphosphine oxide (TOPO) in squalane coated on previously deactivated Chromosorb W. Experimental data fit to a 1:1 alcohol-TOPO association model, with association constants ranging from 26 to 59 dm3 mol(-1) at 45 degrees C. Association constants follow the trend primary alcohols>secondary alcohols>tertiary alcohols, with minor differences between the members of each of these three groups. The association enthalpy for the 21 alcohols averages -21.8 kJ mol(-1), with a standard deviation of -1.3 kJ mol(-1).
Castells
R C
RC
División de Química Analítica, Facultad de Ciencias Exactas, Universidad Nacional de La Plata, Argentina. rcastell@dalton.quimica.unlp.edu.ar
Romero
L M
LM
Nardillo
A M
AM
D000438:Alcohols / Q000737:chemistry*; D002849:Chromatography, Gas / Q000379:methods*; D006860:Hydrogen Bonding; D009943:Organophosphorus Compounds / Q000737:chemistry*
D000438:Alcohols; D009943:Organophosphorus Compounds; C044965:trioctyl phosphine oxide