ABSTRACT

The solid phase behavior of a series of monosubstituted F-, Cl-, Br-, I-, and CH3- and two 2,4-halogen-disubstituted 2-hydroxy-2-phenylacetic acid (mandelic acid) derivatives was investigated. The study includes detailed information about melting temperature, melting enthalpy, X-ray diffraction data, as well as selected binary phase diagrams of the respective chiral systems. Aside from the known metastable conglomerate 2-chloromandelic acid, evidence for two more metastable conglomerates was found.

Compounds

#	Formula	Name
1	C8H7ClO3	2-(4-chlorophenyl)-2-hydroxyacetic acid
2	C8H7ClO3	(S)-2-(4-chlorophenyl)-2-hydroxyacetic acid
3	C8H7BrO3	2-(2-bromophenyl)-2-hydroxyacetic acid
4	C8H7BrO3	(S)-2-(2-bromophenyl)-2-hydroxyacetic acid
5	C8H7BrO3	2-(3-bromophenyl)-2-hydroxyacetic acid
6	C8H7BrO3	(S)-2-(3-bromophenyl)-2-hydroxyacetic acid
7	C8H7BrO3	2-(4-bromophenyl)-2-hydroxyacetic acid
8	C8H7BrO3	(S)-2-(4-bromophenyl)-2-hydroxyacetic acid
9	C8H7IO3	2-hydroxy-2-(2-iodophenyl)acetic acid
10	C8H7IO3	2-hydroxy-2-(3-iodophenyl)acetic acid
11	C8H7IO3	2-hydroxy-2-(4-iodophenyl)acetic acid
12	C9H10O3	2-hydroxy-2-(o-tolyl)acetic acid
13	C9H10O3	2-hydroxy-2-(m-tolyl)acetic acid
14	C9H10O3	(S)-2-hydroxy-2-(m-tolyl)acetic acid
15	C9H10O3	2-hydroxy-2-(p-tolyl)acetic acid
16	C9H10O3	(S)-2-hydroxy-2-(p-tolyl)acetic acid
17	C8H6ClFO3	2-chloro-4-fluoromandelic acid
18	C8H6ClFO3	(S)-2-(2-chloro-4-fluorophenyl)-2-hydroxyacetic acid
19	C8H6ClFO3	2-(4-chloro-2-fluorophenyl)-2-hydroxyacetic acid
20	C8H6ClFO3	(S)-2-(4-chloro-2-fluorophenyl)-2-hydroxyacetic acid
21	C9H10O3	(R)-2-hydroxy-2-(m-tolyl)acetic acid
22	C8H7BrO3	(R)-2-(3-bromophenyl)-2-hydroxyacetic acid
23	C8H7BrO3	(R)-2-(2-bromophenyl)-2-hydroxyacetic acid

Datasets

The table above is generated from the ThermoML associated json file (link above). POMD and RXND refer to PureOrMixture and Reaction Datasets. The compound numbers are included in properties, variables, and phases, if specificied; the numbers refer to the table of compounds on the left.
Type	Compound-#	Property	Variable	Constraint	Phase	Method	#Points
POMD	1	Normal melting temperature, K ; Crystal			Crystal Liquid Air at 1 atmosphere	DTA	1
POMD	1	Molar enthalpy of transition or fusion, kJ/mol ; Crystal			Crystal Liquid Air at 1 atmosphere	DSC	1
POMD	2	Normal melting temperature, K ; Crystal			Crystal Liquid Air at 1 atmosphere	DTA	1
POMD	2	Molar enthalpy of transition or fusion, kJ/mol ; Crystal			Crystal Liquid Air at 1 atmosphere	DSC	1
POMD	3	Normal melting temperature, K ; Crystal			Crystal Liquid Air at 1 atmosphere	DTA	1
POMD	3	Molar enthalpy of transition or fusion, kJ/mol ; Crystal			Crystal Liquid Air at 1 atmosphere	DSC	1
POMD	4	Normal melting temperature, K ; Crystal			Crystal Liquid Air at 1 atmosphere	DTA	1
POMD	4	Molar enthalpy of transition or fusion, kJ/mol ; Crystal			Crystal Liquid Air at 1 atmosphere	DSC	1
POMD	5	Normal melting temperature, K ; Crystal			Crystal Liquid Air at 1 atmosphere	DTA	1
POMD	5	Molar enthalpy of transition or fusion, kJ/mol ; Crystal			Crystal Liquid Air at 1 atmosphere	DSC	1
POMD	6	Normal melting temperature, K ; Crystal			Crystal Liquid Air at 1 atmosphere	DTA	1
POMD	6	Molar enthalpy of transition or fusion, kJ/mol ; Crystal			Crystal Liquid Air at 1 atmosphere	DSC	1
POMD	7	Normal melting temperature, K ; Crystal			Crystal Liquid Air at 1 atmosphere	DTA	1
POMD	7	Molar enthalpy of transition or fusion, kJ/mol ; Crystal			Crystal Liquid Air at 1 atmosphere	DSC	1
POMD	8	Normal melting temperature, K ; Crystal			Crystal Liquid Air at 1 atmosphere	DTA	1
POMD	8	Molar enthalpy of transition or fusion, kJ/mol ; Crystal			Crystal Liquid Air at 1 atmosphere	DSC	1
POMD	9	Normal melting temperature, K ; Crystal			Crystal Liquid Air at 1 atmosphere	DTA	1
POMD	9	Molar enthalpy of transition or fusion, kJ/mol ; Crystal			Crystal Liquid Air at 1 atmosphere	DSC	1
POMD	10	Normal melting temperature, K ; Crystal			Crystal Liquid Air at 1 atmosphere	DTA	1
POMD	10	Molar enthalpy of transition or fusion, kJ/mol ; Crystal			Crystal Liquid Air at 1 atmosphere	DSC	1
POMD	11	Normal melting temperature, K ; Crystal			Crystal Liquid Air at 1 atmosphere	DTA	1
POMD	11	Molar enthalpy of transition or fusion, kJ/mol ; Crystal			Crystal Liquid Air at 1 atmosphere	DSC	1
POMD	12	Normal melting temperature, K ; Crystal			Crystal Liquid Air at 1 atmosphere	DTA	1
POMD	12	Molar enthalpy of transition or fusion, kJ/mol ; Crystal			Crystal Liquid Air at 1 atmosphere	DSC	1
POMD	13	Normal melting temperature, K ; Crystal			Crystal Liquid Air at 1 atmosphere	DTA	1
POMD	13	Molar enthalpy of transition or fusion, kJ/mol ; Crystal			Crystal Liquid Air at 1 atmosphere	DSC	1
POMD	14	Normal melting temperature, K ; Crystal			Crystal Liquid Air at 1 atmosphere	DTA	1
POMD	14	Molar enthalpy of transition or fusion, kJ/mol ; Crystal			Crystal Liquid Air at 1 atmosphere	DSC	1
POMD	15	Normal melting temperature, K ; Crystal			Crystal Liquid Air at 1 atmosphere	DTA	1
POMD	15	Molar enthalpy of transition or fusion, kJ/mol ; Crystal			Crystal Liquid Air at 1 atmosphere	DSC	1
POMD	16	Normal melting temperature, K ; Crystal			Crystal Liquid Air at 1 atmosphere	DTA	1
POMD	16	Molar enthalpy of transition or fusion, kJ/mol ; Crystal			Crystal Liquid Air at 1 atmosphere	DSC	1
POMD	17	Normal melting temperature, K ; Crystal			Crystal Liquid Air at 1 atmosphere	DTA	1
POMD	17	Molar enthalpy of transition or fusion, kJ/mol ; Crystal			Crystal Liquid Air at 1 atmosphere	DSC	1
POMD	18	Normal melting temperature, K ; Crystal			Crystal Liquid Air at 1 atmosphere	DTA	1
POMD	18	Molar enthalpy of transition or fusion, kJ/mol ; Crystal			Crystal Liquid Air at 1 atmosphere	DSC	1
POMD	19	Normal melting temperature, K ; Crystal			Crystal Liquid Air at 1 atmosphere	DTA	1
POMD	19	Molar enthalpy of transition or fusion, kJ/mol ; Crystal			Crystal Liquid Air at 1 atmosphere	DSC	1
POMD	20	Normal melting temperature, K ; Crystal			Crystal Liquid Air at 1 atmosphere	DTA	1
POMD	20	Molar enthalpy of transition or fusion, kJ/mol ; Crystal			Crystal Liquid Air at 1 atmosphere	DSC	1
POMD	21 14	Eutectic composition: mole fraction - 14 ; Crystal - 14			Crystal - 14 Crystal of intercomponent compound 1 Liquid Air at 1 atmosphere	Derived from phase diagram analysis	1
POMD	21 14	Eutectic temperature, K ; Crystal of intercomponent compound 1			Crystal of intercomponent compound 1 Crystal - 14 Liquid Air at 1 atmosphere	DTA	1
POMD	21 14	Solid-liquid equilibrium temperature, K ; Liquid	Mole fraction - 14; Liquid	Pressure, kPa; Liquid	Liquid Crystal - 14	DTA	6
POMD	21 14	Solid-liquid equilibrium temperature, K ; Liquid	Mole fraction - 14; Liquid Pressure, kPa; Liquid		Liquid Crystal of intercomponent compound 1	DTA	1
POMD	22 6	Eutectic composition: mole fraction - 6 ; Crystal - 6			Crystal - 6 Crystal of intercomponent compound 1 Liquid Air at 1 atmosphere	Derived from phase diagram analysis	1
POMD	22 6	Eutectic temperature, K ; Crystal of intercomponent compound 1			Crystal of intercomponent compound 1 Crystal - 6 Liquid Air at 1 atmosphere	DTA	1
POMD	22 6	Solid-liquid equilibrium temperature, K ; Liquid	Mole fraction - 6; Liquid	Pressure, kPa; Liquid	Liquid Crystal of intercomponent compound 1	DTA	7
POMD	22 6	Solid-liquid equilibrium temperature, K ; Liquid	Mole fraction - 6; Liquid	Pressure, kPa; Liquid	Liquid Crystal - 6	DTA	2
POMD	23 4	Eutectic composition: mole fraction - 4 ; Crystal - 23			Crystal - 23 Crystal - 4 Liquid Air at 1 atmosphere	Derived from phase diagram analysis	1
POMD	23 4	Eutectic temperature, K ; Crystal - 23			Crystal - 23 Crystal - 4 Liquid Air at 1 atmosphere	DTA	1
POMD	23 4	Solid-liquid equilibrium temperature, K ; Liquid	Mole fraction - 4; Liquid Pressure, kPa; Liquid		Liquid Crystal - 23	DTA	1
POMD	23 4	Solid-liquid equilibrium temperature, K ; Liquid	Mole fraction - 4; Liquid	Pressure, kPa; Liquid	Liquid Crystal - 4	DTA	8

Thermodynamics Research Center / ThermoML | Journal of Chemical and Engineering Data

Solid Phase Behavior in the Chiral Systems of Various 2-Hydroxy-2-phenylacetic Acid (Mandelic Acid) Derivatives

Von Langermann, J.[Jan], Temmel, E.[Erik], Seidel-Morgenstern, A.[Andreas], Lorenz, H.[Heike]

ABSTRACT