Unusually low barrier to carbamate C-N rotation.

No abstract is available for this paper.

• Publication year

  2002

• Venue

  Journal of Organic Chemistry

• Publication date

  2002-04-30

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1021/JO025554UPMID 12027723
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

• Using Hydrogen Bonding to Control Carbamate C-N Rotamer Equilibria.

  1998cited by this paper
• Polyene macrolide antibiotic amphotericin B. Crystal structure of the N-iodoacetyl derivative.

  1971cited by this paper
• Stereochemistry of Organic Compounds

  1962cited by this paper

• cisPro stabilization in prolyl carbamates influenced by tetrel bonding interactions.

  2024cites this paper
• Synthesis and full characterization of tert-butyl (4-ethynylphenyl)carbamate

  2024cites this paper
• VT‐NMR Analysis of Rotation‐Inversion of N‐(4‐hydroxybutyl)‐N‐(2,2,2‐trifluoroethyl) tert‐butyl Carbamate: Utilizing the −CH2CF3 Appendage as a Reporter on E/Z‐Isomerization

  2024cites this paper
• Metabolically activated proteostasis regulators that protect against erastin-induced ferroptosis

  2024cites this paper
• Promising Inhibitors of Endocannabinoid Degrading Enzymes Sharing a Carbamate Scaffold.

  2024cites this paper
• Rotation-Inversion Isomerization of Tertiary Carbamates: Potential Energy Surface Analysis of Multi-Paths Isomerization Using Boltzmann Statistics.

  2022cites this paper
• o-(2-Thienyl)vinylarene as an Alternative Synthetic Motif for Porphyrinoids: o-Arene-Connected Porphyrinoids.

  2022cites this paper
• Insights into the Role of Hydrogen Bonds on the Mechanical Properties of Polymer Networks

  2021cites this paper
• Alternative and efficient method for the preparation of 2-acetamidobenzimidazoles

  2021cites this paper
• Spectral evidence for generic charge → acceptor interactions in carbamates and esters

  2020cites this paper
• 2,3-Diaminopropanols Obtained from d-Serine as Intermediates in the Synthesis of Protected 2,3-l-Diaminopropanoic Acid (l-Dap) Methyl Esters

  2020cites this paper
• Carbamate Group as Structural Motif in Drugs: A Review of Carbamate Derivatives used as Therapeutic Agents

  2020cites this paper
• Novel dauricine derivatives suppress cancer via autophagy-dependent cell death.

  2019cites this paper
• Modification of Biodistribution and Brain Uptake of Copper Bis(thiosemicarbazonato) Complexes by the Incorporation of Amine and Polyamine Functional Groups.

  2019cites this paper
• Hindered C–N bond rotation in triazinyl dithiocarbamates

  2018cites this paper
• Visible-light photocatalyzed oxidative decarboxylation of oxamic acids: a green route to urethanes and ureas.

  2018cites this paper
• N bond rotation in triazinyl dithiocarbamates

  2017cites this paper
• Structural systematics and conformational analyses of an isomer grid of nine tolyl-N-pyridinylcarbamates

  2017cites this paper
• Catalysts and temperature driven melt polycondensation reaction for helical poly(ester-urethane)s based on natural L-amino acids

  2016cites this paper
• 3-Oxoisoxazole-2(3H)-carboxamides and isoxazol-3-yl carbamates: Resistance-breaking acetylcholinesterase inhibitors targeting the malaria mosquito, Anopheles gambiae.

  2015cites this paper
• Pairwise Packing of Anthracene Fluorophore: Hydrogen-Bonding-Assisted Dimer Emission in Solid State

  2015cites this paper
• Organic Carbamates in Drug Design and Medicinal Chemistry

  2015cites this paper
• Selective Silylative Reduction of Pyridines Leading to Structurally Diverse Azacyclic Compounds with the Formation of sp³ C-Si Bonds.

  2015cites this paper
• Understanding the directed ortho lithiation of (R)-Ph₂P(=NCO₂Me)NHCH(Me)Ph. NMR spectroscopic and computational study of the structure of the N-lithiated species.

  2014cites this paper
• Conformation analysis and computation of energy barrier to rotation about CN bond in para-methylphenyl carbamate and its solvent dependence in comparison with tertiary carbamates and tertiary amides

  2014cites this paper
• Synthesis and Dynamic NMR Studies of Some New Symmetrical Podands of Dithiocarbamates Formed from Bis(N-thiazol)chloroacetamides

  2013cites this paper
• Activation of isocyanates and carbon dioxide by a monomeric aluminium hydrazide as an active Lewis pair.

  2013cites this paper
• Rotational isomers of N-methyl-N-arylacetamides and their derived enolates: implications for asymmetric Hartwig oxindole cyclizations.

  2013cites this paper
• Hindered Rotation in Some Organic Dithiocarbamates

  2013cites this paper
• A Simple and Eco-Compatible One-Pot Synthesis of New Symmetrical Dithiocarbamate Podands and Their Dynamic NMR Studies

  2013cites this paper
• O-perfluoroalkyl thiocarbamates: Synthesis and perfluoroalkyl effects on the barrier to NCS rotation

  2013cites this paper
• N-arylamides and N-arylcarbamates NCO internal rotation barrier study by molecular modeling

  2012cites this paper
• A simple and efficient synthesis and dynamic NMR studies of some new podands of dithiocarbamates formed from bis(naphthyl) derivatives

  2011cites this paper
• A paradigm for solvent and temperature induced conformational changes.

  2011cites this paper
• Synthesis of 2-Arylethylamines by the Curtius Rearrangement

  2010cites this paper
• Importance of C-N bond rotation in N-acyl oxazolidinones in their SmI2-promoted coupling to acrylamides.

  2009cites this paper
• C-N bond rotation and E-Z isomerism in some N-benzyl-N-methylcarbamoyl chlorides : A DFT study

  2008cites this paper
• Medium effect on the rotational barrier of carbamates and its sulfur congeners.

  2007cites this paper
• Transesterification and amide cis-trans isomerization in Zn and Cd complexes of the chelating amino acid ligand Boc-Asp(Dpa)-OBzl.

  2007cites this paper
• Investigation of the barrier to the rotation of carbamate and amide C–N bonds in antidepressant (6aR∗,11bS∗)-7-[carbobenzyloxy-l-alanyl]-2-[(4-methylphenyl)sulfonyl]-1,2,3,4,6,6a,7,11b,2,12a(S)-decahydropyrazino[2′,1′:6,1]pyrido[3,4-b]indole by dynamic NMR and molecular mechanics

  2007cites this paper
• Stereoselektive Synthese neuartiger 1,2-Dihydroisochinoline als Vorstufen für die Alkaloidsynthese

  2007cites this paper
• Cis/trans configurations of the peptide CN bonds: isomerization and photoswitching

  2007cites this paper
• Dynamic 1H NMR study of the barrier to rotation about the C-N bond in primary carbamates and its solvent dependence.

  2007cites this paper
• Experimental and theoretical investigation of the IR spectra and thermochemistry of four isomers of 2-N,N-dimethylaminecyclohexyl 1-N’,N’-dimethylcarbamate

  2006cites this paper
• The profound effect of fluorine substitution on the reactivity and regioselectivity of nucleophilic substitution reactions of strained heterocycles. A study of aziridine and its derivatives.

  2006cites this paper
• An unprecedented radical ring closure on a pyridine nitrogen.

  2006cites this paper
• Separation and HPLC Analysis of Diastereomers and Rotational Isomers of L‐N‐(Butyloxycarbonyl)‐3‐(3‐Hydroxyethyl‐4‐(Benzyloxy)‐Phenyl) Alanine Benzyl Ester

  2006cites this paper
• A simple and efficient biphasic method for the preparation of 4-nitrophenyl N-methyl- and N-alkylcarbamates

  2006cites this paper
• NMR and theoretical study of the (CO)–N rotational barrier in the isomers cis- and trans- 2-N,N-dimethylaminecyclohexyl 1-N′,N′-dimethylcarbamate

  2005cites this paper
• Structural variability and dynamics in carboxylato- and carbamatomagnesium bromides. Relationship to the carboxylate shift.

  2005cites this paper
• Evidence for unimolecular CO2 elimination in C-N bond metathesis reactions of basic carbamatozinc complexes Zn4O(O2CAm)6(Am=N-diethylamino, N-piperidyl, N-pyrrolidyl).

  2005cites this paper
• Amide resonance in thio- and seleno- carbamates: A theoretical study

  2005cites this paper
• Conversion of five-, six-, and seven-membered lactams to racemic or scalemic 2-substituted heterocycles by amidoalkylation.

  2005cites this paper
• Conformational preferences and self-template macrocyclization of squaramide-based foldable modules.

  2004cites this paper
• Substituent effects on the barrier to carbamate C–N rotation

  2004cites this paper
• Dynamic NMR and ab initio studies of exchange between rotamers of derivatives of octahydrofuro[3,4‐f]isoquinoline‐7(1H)‐carboxylate and tetrahydro‐2,5,6(1H)‐isoquinolinetricarboxylate

  2004cites this paper
• Cis-trans isomerization of organic molecules and biomolecules: implications and applications.

  2003cites this paper
• Conformational analysis of N-boc-N, O-isopropylidene-α-serinals. A combined DFT and NMR study

  2003cites this paper