A remarkably high specific rotation, even at 589 nm, is shown by (M)-1, the first enantiomerically pure unbranched [4]triangulane, although it has no chromophore that would lead to any significant absorption above 200 nm. This outstanding rotatory power is in line with a helical arrangement of its sigma bonds, as confirmed by high-level computations. Thus, it is appropriate to call (M)-1 a "sigma-[4]helicene", the first sigma-bond analogue of the aromatic [n]helicenes.
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http://dx.doi.org/10.1002/(sici)1521-3773(19991203)38:23<3474::aid-anie3474>3.3.co;2-y | DOI Listing |
Molecules
January 2025
Instituto de Síntesis Química y Catálisis Homogénea, ISQCH (CSIC-Universidad de Zaragoza), Pedro Cerbuna 12, 50009 Zaragoza, Spain.
Orthopalladated derivatives from substituted phenylglycines [Pd(μ-Cl)(CHRC(R)(R)N(R)] () react with halogenating reagents (PhICl, Br, I) () to give the corresponding o-halogenated amino acids CH(X)RC(R)(R)N(R) (). The reaction is general and tolerates a variety of functional groups (R to R) at the aryl ring, the Cα, and the N atom. On the other hand, the reaction of [Pd(μ-Cl)(CHRC(R)(R)N(R)] () with PhI(OAc) in the presence of a variety of alcohols ROH () gives the o-alkoxylated phenylglycines CH(OR)RC(R)(R)N(R) (), also as a general process.
View Article and Find Full Text PDFBiomolecules
January 2025
United States Department of Agriculture-Agricultural Research Service (USDA-ARS), Subtropical Horticulture Research Station (SHRS), Miami, FL 33158, USA.
Tea tree oil (TTO), acquired from (Maiden & Betche) Cheel, Myrtaceae, is a widely utilized essential oil (EO) due to its bioactive properties. The identification and quantification of TTO ingredients is generally performed by GC-MS, which provides the most accurate results. However, in some instances, the cost and time of analysis may pose a challenge.
View Article and Find Full Text PDFActa Crystallogr C Struct Chem
February 2025
Departamento de Química Inorgánica, Analítica y Química Física, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Intendente Güiraldes 2160, Piso 3, Ciudad Universitaria, C1428EGA Buenos Aires, Argentina.
In this study, we present a new N-derivative of L-phenylalanine with 2-naphthaldehyde (PN), obtained by the Schiff base formation procedure and its subsequent reduction. This compound was crystallized as a zwitterion {2-[(naphthalen-2-ylmethyl)azaniumyl]-3-phenylpropanoate, CHNO}, as an anion in a sodium salt (catena-poly[[diaquasodium(I)-di-μ-aqua] 2-[(naphthalen-2-ylmethyl)amino]-3-phenylpropanoate monohydrate], {[Na(HO)](CHNO)·HO}), as a cation in a chloride salt [(1-carboxy-2-phenylethyl)(naphthalen-2-ylmethyl)azanium chloride acetic acid monosolvate, CHNO·Cl·CHCOOH], and additionally acting as a ligand in the pentacoordinated zinc compound aquabis{2-[(naphthalen-2-ylmethyl)amino]-3-phenylpropanoato-κO}zinc(II), [Zn(CHNO)(HO)] or [Zn(PN)(HO)], denoted (PN-Zn), with the amino acid derivative in its carboxylate form.
View Article and Find Full Text PDFChirality
February 2025
Department of Chemistry, Bogazici University, Istanbul, Turkey.
2-Thiohydantoin derivatives, including different substitutions at N-1 and C-5 (5-methyl-, 5-isopropyl-, 1-acetyl-5-methyl-, and 1-acetyl-5-isopropyl-) (1-4, respectively), were synthesized by the known literature methods. In these synthetic pathways, it was reported that enantiomerically pure 2-thiohydantions were obtained in the absence of any solvent via the reaction of L-amino acids with thiourea (1&2) and via the reaction of L-amino acids with NHSCN and acetic anhydride (3&4). However, in this study, in contrary to the previous literature studies, racemic mixtures of 2-thiohydantoins were obtained although the same synthetic methods were used.
View Article and Find Full Text PDFJ Am Chem Soc
January 2025
Department of Chemistry, University of Florida, Gainesville, Florida 32611, United States.
Precisely controlling quantum states is relevant in next-generation quantum computing, encryption, and sensing. Chiral organic chromophores host unique light-matter interactions, which allow them to manipulate the quantized circular polarization of photons. Axially chiral organic scaffolds, such as helicenes or twisted acenes, are powerful motifs in chiral light manipulation.
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