GC-MS Study of Mono- and Bishaloethylphosphonates Related to Schedule 2.B.04 of the Chemical Weapons Convention: The Discovery of a New Intramolecular Halogen Transfer.
A new class of compounds, mono- and bis-haloethylphosphonates (HAPs and bisHAPs, respectively), listed in Schedule 2.B.04 of the Chemical Weapons Convention (CWC), has been synthesized and studied by GC-MS with two aims. First, to improve the identification of this type of chemicals by the Organization for the Prohibition of Chemical Weapons, (OPCW). Second, to study the synergistic effect of halogen and silicon atoms in molecules undergoing mass spectrometry. Fragmentation patterns of trimethylsilyl derivatives of HAPs were found to depend on the nature of the halogen atom; this was in agreement with DFT-calculations. The data suggest that a novel intramolecular halogen transfer takes place during the fragmentation process. Graphical Abstract ᅟ.
Ingeniería de Sistemas para la Defensa de España (ISDEFE), Beatriz de Bobadilla 3, E-28040, Madrid, Spain.
Nerea
N
Picazas-Márquez
Ingeniería de Sistemas para la Defensa de España (ISDEFE), Beatriz de Bobadilla 3, E-28040, Madrid, Spain.
María
M
Sierra
Ingeniería de Sistemas para la Defensa de España (ISDEFE), Beatriz de Bobadilla 3, E-28040, Madrid, Spain.
Clara
C
Nova
Laboratorio de Verificación de Armas Químicas (LAVEMA), Área de Defensa Química, Subdirección General de Sistemas Terrestres, INTA, Campus La Marañosa, San Martín de la Vega, E-28330, Madrid, Spain.
Juan Manuel
JM
Moreno
Ingeniería de Sistemas para la Defensa de España (ISDEFE), Beatriz de Bobadilla 3, E-28040, Madrid, Spain.
Nuria
N
Aboitiz
Laboratorio de Verificación de Armas Químicas (LAVEMA), Área de Defensa Química, Subdirección General de Sistemas Terrestres, INTA, Campus La Marañosa, San Martín de la Vega, E-28330, Madrid, Spain.
Gema
G
de Rivas
Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Complutense, E-28040, Madrid, Spain.
Miguel A
MA
Sierra
Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Complutense, E-28040, Madrid, Spain. rma@quim.ucm.es.
Roberto
R
Martínez-Álvarez
Laboratorio de Verificación de Armas Químicas (LAVEMA), Área de Defensa Química, Subdirección General de Sistemas Terrestres, INTA, Campus La Marañosa, San Martín de la Vega, E-28330, Madrid, Spain.
Esther
E
Gómez-Caballero
Chemical weapons convention; Haloethylphosphonates; Iodine transfer