naa a22 4500 510734340 CHVBK 20180411083004.0 cr unu---uuuuu 180411e20130701xx s 000 0 eng 10.1007/s12039-013-0466-y doi (NATIONALLICENCE)springer-10.1007/s12039-013-0466-y Theoretical study of intramolecular hydrogen bonding in the halo derivatives of 1-amino-3-imino-prop-1-ene [Elektronische Daten] [SAEEDREZA EMAMIAN, SAYYED TAYYARI] Intramolecular hydrogen bonding (IHB) of 1-amino-3-imino-prop-1-ene (AIP), as the simplest resonance-assisted hydrogen bond system in symmetric N-H···N class, and its halo derivatives (F, Cl, and Br) have been studied at the DFT-B3LYP/6-311+ +G ∗ ∗  level of theory. For better understanding of the nature of substituent effects, nitro and methoxy derivatives of AIP were also added to our consideration. Good linear correlations between IHB energies based on Espinosa's equation and − G(r)/V(r) values, total electronic density, Laplacian of total electronic density in critical points, π-electron delocalization parameter (Q), hyper conjugative interaction energy of lp(N) $\to \upsigma ^{\ast}$ (N-H), ( $F_{i,j}/S_{i,j})^{2}$ parameter, natural charges of bridged hydrogen, frequency shift of the N-H stretching vibration, and chemical shift of bridged hydrogen were obtained. Graphical Abstract In the present study, halo (F, Cl, and Br) as well as nitro and methoxy substituent effect on the intramolecular hydrogen bonding strength of 1-amino-3-iminoprop- 1-ene as the simplest resonance-assisted hydrogen bond system in symmetric N-H⋯N class is theoretically investigated at the B3LYP/6-31++G** level using various identifying indexes. Indian Academy of Sciences, 2013 Intramolecular hydrogen bond nationallicence 1-amino-3-imino-prop-1-ene (AIM) nationallicence density functional theory (DFT) nationallicence natural bond orbital analysis (NBO) nationallicence EMAMIAN SAEEDREZA Department of Chemistry, Shahrood Branch, Islamic Azad University, Shahrood, Iran aut TAYYARI SAYYED Department of Chemistry, Shahrood Branch, Islamic Azad University, Shahrood, Iran aut Journal of Chemical Sciences Springer India 125/4(2013-07-01), 939-948 0974-3626 125:4<939 2013 125 12039 https://doi.org/10.1007/s12039-013-0466-y text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/s12039-013-0466-y text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- EMAMIAN SAEEDREZA Department of Chemistry, Shahrood Branch, Islamic Azad University, Shahrood, Iran aut NATIONALLICENCE 700 1- TAYYARI SAYYED Department of Chemistry, Shahrood Branch, Islamic Azad University, Shahrood, Iran aut NATIONALLICENCE 773 0- Journal of Chemical Sciences Springer India 125/4(2013-07-01), 939-948 0974-3626 125:4<939 2013 125 12039 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer