Five relatedN′-(2,2,2-trichloroethanimidoyl)benzene-1-carboximidamides

Abstract

In the solid state, 4-methoxy-N'-(2,2,2-trichloroethanimidoyl)benzene-1-carboximidamide, C(10)H(10)Cl(3)N(3)O, (I), N'-(2,2,2-trichloroethanimidoyl)benzene-1-carboximidamide, C(9)H(8)Cl(3)N(3), (II), 4-chloro-N'-(2,2,2-trichloroethanimidoyl)benzene-1-carboximidamide, C(9)H(7)Cl(4)N(3), (III), 4-bromo-N'-(2,2,2-trichloroethanimidoyl)benzene-1-carboximidamide, C(9)H(7)BrCl(3)N(3), (IV), and 4-trifluoromethyl-N'-(2,2,2-trichloroethanimidoyl)benzene-1-carboximidamide, C(10)H(7)Cl(3)F(3)N(3), (V), display strong intramolecular N-H...N hydrogen bonding across the chelate ring and also intramolecular N-H...Cl contacts. Additional intermolecular hydrogen bonds link the molecules into chains, double chains or sheets in all cases except for compound (V). For compound (II), there are three independent molecules per asymmetric unit.

4-Methyl-N′-(2,2,2-trichloroethanimidoyl)benzene-1-carboximidamide

“…The title compound (Figure 1), commonly known as an imidoylamidine, was prepared as part of our continuing interest in C,N,S based heterocycles (Boeré, Roemmele & Yu, 2011). The molecular structure is very similar to seven independent molecules from our prevous study (Boeré, Roemmele, Suduweli Kondage et al, 2011), with only a single tautomeric form being evidenced in the crystal lattice. The bond lengths and angles for the NÛ CÛNÛCÛN core are nearly identical within the s.u.…”

Resonance‐Assisted Hydrogen Bonding as a Driving Force in Synthesis and a Synthon in the Design of Materials

“…E/Z isomerization of formazans. 2016 [234] Donor-acceptor N(H)···N distances for the RAHB system are in the range of 2.616(2)-2.657 (4) .H owever,t here was no correlation between the Hammett's s p substituent constant [180] and the NÀN distances (Scheme 33). Synthesis of 3-cyanoformazans.…”

“…Thus, with respect to stability and as a driving force in the synthesis of 1,3,5‐triazapenta‐1,3‐dienes, the U form with a strong RAHB system is of special interest. For example, a series of 1,3,5‐triazapenta‐1,3‐dienes was prepared by addition of 2,2,2‐trichloroacetonitrile to the corresponding para ‐substituted benzamidines in acetonitrile, displaying strong intramolecular N−H⋅⋅⋅N RAHB interactions across the ring (Scheme ) . Donor–acceptor N(H)⋅⋅⋅N distances for the RAHB system are in the range of 2.616(2)–2.657(4) Å.…”

Dispersion in Crystal Structures of 1-Chloro-3-aryl-5-trihalomethyl-1λ4,2,4,6-thiatriazines: Towards an Understanding of the Supramolecular Organization of Covalent Thiazyl Chlorides

“…Full synthetic and characterization details for the starting aryl/trichloromethyl imidoylamidines, 1 , are provided in the Supporting Information (Sections S1 and S2; Tables S1–S3; Figure S1), and the SC-XRD of these key starting materials have previously been published. 29 30 These versatile nitrogen-rich reagents were first passivated by protonation with anhydrous hydrogen chloride in ether, and then the dried powders of 2 were immediately suspended in highly purified and rigorously dry acetonitrile, reacted with an excess of freshly distilled sulfur dichloride, and then heated to reflux until HCl evolution ceased. Concentration and cooling of the solutions enabled the direct growth of pure crystals suitable for SC-XRD (see below), whilst bulk product was obtained by removal of all volatiles and recrystallization from hot, dry, n -heptane.…”