Naslov
Intermolecular interactions in two cyclic amidino-derivatives built three-dimensional network

Autori
Cetina, Mario ; Ptiček, Lucija ; Racane, Livio

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
The Twenty-Sixth Croatian-Slovenian Crystallographic Meeting / Matković-Čalogović, Dubravka ; Popović, Stanko ; Skoko, Željko - Zagreb : Hrvatska akademija znanosti i umjetnosti (HAZU) ; Hrvatska Kristalografska Zajednica, 2018, 22-22

Skup
26th Croatian-Slovenian Crystallographic Meeting (CSCM26)

Mjesto i datum
Poreč, Hrvatska, 13.06.2018. - 17.06.2018

Vrsta sudjelovanja
Predavanje

Vrsta recenzije
Nije recenziran

Ključne riječi
amidino-derivatives ; benzoxazoles ; 2-aminophenols ; intermolecular interactions

Sažetak
In contrast to a great number of biologically active amidino-substituted benzimidazole and benzothiazole derivatives, benzoxazoles are still rare. The main reason is the lack of a general method for their preparation, which could be based on a condensation reaction of the amidino-substituted 2-aminophenols with aldehydes, carboxylic acids and carboxylic acid derivatives as commercially available substrates. In our last contribution, we presented synthesis of unsubstituted, N-substituted and cyclic amidino-derivatives [1]. Herein we present crystal structures of two new cyclic amidino-derivatives of 2-aminophenols as the key building blocks for the synthesis of amidino-substituted benzoxazoles. Structures of two cyclic amidino-derivatives are shown in Figure 1. Compound 1 crystallized as monohydrate in zwitterionic form with equal C7-N2 and C7-N3 bond lengths, typically for amidino moiety. Crystals of compound 2, which also crystallized as monohydrate, were obtained in the methanesulfonate salt form, but not as zwitterion. Nitrogen N1 atom in this compound is protonated, and therefore there are two methanesulfonate anions in the structure. As in 1, amidino moiety is confirmed by almost equivalent C7-N2 and C7-N3 bond lengths. Supramolecular structures of 1 and 2 contain a number of various intermolecular interactions (O-H···O, N-H···O, O-H···N and C-H···O hydrogen bonds, as well as C−H···Pi and Pi···Pi interactions) that built three-dimensional network. References [1] L. Ptiček, M. Cetina, M. Mudrešić and L. Racané, Synthesis and structural analysis of novel isomeric amidino-substituted 2-aminophenols, 25th Croatian Meeting of Chemists and Chemical Engineers, Poreč, April 19-22, 2017.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA