The Unimolecular Chemistry of Methyl Chloroformate Ions and Neutrals : a Story of Near-Threshold Decomposition

Lowe, Bethany - Cardona, Alejandro L. - Bodi, Andras - Mayer, Paul M. - Burgos Paci, Maxi A.

Resumen:

The near threshold dissociation of ionized and neutral methyl chloroformate (CH3COOCl, MCF) was explored with imaging photoelectron photoion coincidence spectroscopy. The threshold photoelectron spectrum (TPES) for MCF was acquired for the first time; the large geometry changes upon ionization of MCF results in a broad, poorly defined TPES. Franck–Condon simulations are consistent with an adiabatic ionization energy (IE) of 10.90 ± 0.05 eV. Ionized MCF dissociates by chlorine atom loss at a measured 0 K appearance energy (AE) of 11.30 ± 0.01 eV. Together with the above IE, this AE suggests a reaction barrier of 0.40 ± 0.05 eV, consistent with the SVECV-f12 computational result of 0.41 eV. At higher internal energies, the loss of CH3O• becomes competitive due to its lower entropy of activation. Pyrolysis of neutral MCF formed the anticipated major products CH3Cl + CO2 (R1) and the minor products HCl + CO + CH2O (R2). The thermal decomposition products were identified by their photoion mass-selected threshold photoelectron spectrum (ms-TPES). Possible reaction pathways were explored computationally to confirm the dominant ones: R1 proceeds by a concerted Cl atom migration via a 4- membered transition state in agreement with the mechanism proposed in the literature. R2 is a twostep reaction first yielding 2-oxiranone by HCl loss, which then decomposes to CH2O and CO. Kinetic modeling of the neutral decomposition could simulate the observed reactions only if the vibrational temperature of the MCF was assumed not to cool in the expansion.

Detalles Bibliográficos
2023
Methyl chloroformate
Imaging photoelectron photoion coincidence spectroscopy
Photoelectron spectroscopy
Pyrolysis
Reaction mechanisms
Computational chemistry
Kinetic modelling
Cloroformiato de metilo
Espectroscopia de coincidencia de fotoiones y fotoelectrones
Espectroscopia fotoelectrónica
Pirólisis
Mecanismos de reacción
Química computacional
Modelado cinético
Inglés
Universidad de la República
COLIBRI
https://hdl.handle.net/20.500.12008/49946
https://doi.org/10.1021/jasms.3c00334
Acceso abierto
Licencia Creative Commons Atribución - No Comercial - Sin Derivadas (CC - By-NC-ND 4.0)