Predictive Models for Halogen-Bond Basicity of Binding Sites of Polyfunctional Moleculesстатья
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Аннотация:Halogen bonding (XB) strength assesses the abili-
ty of an electron-enriched group to be involved in com-
plexes with polarizable electrophilic halogenated or di-
atomic halogen molecules. Here, we report QSPR models of
XB of particular relevance for an efficient screening of large
sets of compounds. The basicity is described by pKBI2, the
decimal logarithm of the experimental 1:1 (B :I2) complexa-
tion constant K of organic compounds (B) with diiodine (I2)
as a reference halogen-bond donor in alkanes at 298 K.
Modeling involved ISIDA fragment descriptors, using SVM
and MLR methods on a set of 598 organic compounds. De-
veloped models were then challenged to make predictions
for an external test set of 11 polyfunctional compounds for
which unambiguous assignment of the measured effective
complexation constant to specific groups out of the puta-
tive acceptor sites is not granted. At this stage, developed
models were used to predict pKBI2of all putative acceptor
sites, followed by an estimation of the predicted effective
complexation constant using the ChemEqui program. The
best consensus models perform well both in cross-valida-
tion (root mean squared error RMSE=0.39–0.47 logKBI2
units) and external predictions (RMSE=0.49). The SVM
models are implemented on our website (http://infochim.u-
strasbg.fr/webserv/VSEngine.html) together with the estima-
tion of their applicability domain and an automatic detec-
tion of potential halogen-bond acceptor atoms.