(2-Azoniaethyl)guanidinium dichloride – A promising phase-matchable NLO material employing a simple hydrogen bond acceptor in its structure

Synthesis of Phosphanylferrocenecarboxamides Bearing Guanidinium Substituents and Their Application in the Palladium‐Catalyzed Cross‐Coupling of Boronic Acids with Acyl Chlorides

“…Ligand 2 possessing an alkylguanidinium pendant and an extended amidoalkyl spacer group was synthesized by two different methods. The first one (route A in Scheme ) made use of the standard amide coupling reaction between 1′‐(diphenylphosphanyl)ferrocene‐1‐carboxylic acid (Hdpf) and N ‐(2‐aminoethyl)guanidine hydrochloride liberated from the respective dihydrochloride with 1 mol‐equiv. of triethylamine.…”

“…Materials and Methods: All manipulations were carried out under argon by using standard Schlenk techniques. Compound 3 , Hdpf, and N ‐(2‐aminoethyl)guanidine dihydrochloride were prepared according to literature procedures. All other chemicals were obtained from commercial sources (Sigma–Aldrich and Alfa‐Aesar) and used as received.…”

The crystal structure of the inner salt of 2-[(aminoiminomethyl)amino]ethylcarbamic acid [systematic name: (2-((diaminomethylene)ammonio)ethyl)carbamate], C4H10N4O2

“…Owing to their delocalized nature (6π electrons in a conjugated planar system), they have also found applications in material science, particularly in the design of non-linear optical materials [5,[8][9][10] and molecular sensors [11][12][13]. In continuation of our studies focused on the nonlinear optical properties of hybrid organic-inorganic materials, we have recently reported the synthesis and detailed characterization of salts comprising (2-azoniaethyl)guanidinium cation and simple inorganic anions (viz.…”

“…A suspension of silver(I) carbonate (322 mg, 1.17 mmol) in 25 mL of deionized water was added to an aqueous solution of (2-azoniaethyl)guanidinium dichloride (204 mg, 1.17 mmol in 5 mL) [5]. The resultant mixture was stirred for 60 min and then filtered to remove precipitated AgCl.…”

“…In continuation of our studies focused on the nonlinear optical properties of hybrid organic-inorganic materials, we have recently reported the synthesis and detailed characterization of salts comprising (2-azoniaethyl)guanidinium cation and simple inorganic anions (viz. Cl − , NO 3 − and ClO4 − ), among which the dichloride exerted favorable nonlinear optical properties [5]. In order to extend the series of these prospective materials, we attempted to prepare the corresponding carbonate or the free base for use in further syntheses.…”