Individual Hydrogen-Bond Strength QSPR Modelling with ISIDA Local Descriptors: a Step Towards Polyfunctional Moleculesстатья
Информация о цитировании статьи получена из
Web of Science,
Scopus
Статья опубликована в журнале из списка Web of Science и/или Scopus
Дата последнего поиска статьи во внешних источниках: 3 декабря 2017 г.
Аннотация:Here, we introduce new ISIDA fragment descrip-
tors able to describe “local” properties related to selected
atoms or molecular fragments. These descriptors have
been applied for QSPR modelling of the H-bond basicity
scale pKBHX, measured by the 1:1 complexation constant of
a series of organic acceptors (H-bond bases) with 4-fluoro-
phenol as the reference H-bond donor in CCl4at 298 K.
Unlike previous QSPR studies of H-bond complexation, the
models based on these new descriptors are able to predict
the H-bond basicity of different acceptor centres on the
same polyfunctional molecule. QSPR models were obtained
using support vector machine and ensemble multiple linear
regression methods on a set of 537 organic compounds in-
cluding 5 bifunctional molecules. They were validated with
cross-validation procedures and with two external test sets.
The best model displays good predictive performance on
a large test set of 451 mono- and bifunctional molecules:
a root-mean squared error RMSE=0.26 and a determination
coefficient R2=0.91. It is implemented on our website
(http://infochim.u-strasbg.fr/webserv/VSEngine.html)
together with the estimation of its applicability domain and
an automatic detection of potential H-bond acceptors.