☆ 4.8 Review

Opportunities and Challenges in Applying Solid-State NMR Spectroscopy in Organic Mechanochemistry

ADVANCED MATERIALS (2023)

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Summary: Mechanochemical processing is an efficient and unique tool for the synthesis and transformation of various materials. Recent advancements combine mechanochemical reactivity with other energy sources, achieving reactions not possible with traditional methods. Thermo-mechanochemistry, sono-mechanochemistry, electro-mechanochemistry, and photo-mechanochemistry represent significant advances in modern mechanochemistry, introducing a new level of solid-state reactivity.

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Summary: This study investigates the various solid forms of Xylazine HCl (X) and explores the reliable preparation and interconversion methods for these forms. It also discovers a novel polymorph and synthesizes three cocrystals. Thermal analysis, X-ray diffraction, and solid-state NMR spectroscopy are used to characterize the materials. 35Cl SSNMR proves to be versatile in fingerprinting polymorphs and detecting features that PXRD cannot show, offering a pathway for optimizing synthetic protocols and providing molecular-level structural information.

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Summary: This study presents a setup that uses mechanochemistry to promote solid-solid interactions and couples it with nuclear magnetic resonance (NMR) to monitor the variation in real time. The system is applied to analyze optically active species responding to self-disproportionation of enantiomers by sublimation and introduces an advanced concept of enantiomer recognition based on selective sublimation.

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Ago Samoson

JOURNAL OF MAGNETIC RESONANCE (2019)

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Article Chemistry, Multidisciplinary

Ettringite via Mechanochemistry: A Green and Rapid Approach for Industrial Application

Julia Stroh et al.

ACS OMEGA (2019)

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Article Chemistry, Inorganic & Nuclear

Looking into the Black Box of Solid-State Synthesis

Holger Kohlmann

EUROPEAN JOURNAL OF INORGANIC CHEMISTRY (2019)

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Article Chemistry, Physical

Influence of Aluminum Addition on the Structure and Feathers of V2O5 Oxide Prepared by Mechanochemical Activation

Alexander I. Kokorin et al.

JOURNAL OF PHYSICAL CHEMISTRY C (2019)

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Article Chemistry, Multidisciplinary

Tuning the Apparent Stability of Polymorphic Cocrystals through Mechanochemistry

Hannes Kulla et al.

CRYSTAL GROWTH & DESIGN (2019)

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Article Spectroscopy

Discriminating polymorph distributions in pharmaceutical tablets using stimulated Raman scattering microscopy

Barbara Sarri et al.

JOURNAL OF RAMAN SPECTROSCOPY (2019)

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Review Chemistry, Multidisciplinary

Mechanochemistry of Gaseous Reactants

Carsten Bolm et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

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Article Medicine, Research & Experimental

Understanding Compression-Induced Amorphization of Crystalline Posaconazole

Chengbin Huang et al.

MOLECULAR PHARMACEUTICS (2019)

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Review Chemistry, Multidisciplinary

From enabling technologies to medicinal mechanochemistry: an eco-friendly access to hydantoin-based active pharmaceutical ingredients

Evelina Colacino et al.

REACTION CHEMISTRY & ENGINEERING (2019)

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Review Chemistry, Organic

Mechanochemistry for Organic Chemists: An Update

Davin Tan et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2018)

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Article Chemistry, Multidisciplinary

Ball-free mechanochemistry: in situ real-time monitoring of pharmaceutical co-crystal formation by resonant acoustic mixing

Adam A. L. Michalchuk et al.

CHEMICAL COMMUNICATIONS (2018)

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Article Chemistry, Multidisciplinary

Mechanochemical dehydrocoupling of dimethylamine borane and hydrogenation reactions using Wilkinson's catalyst

Christian Schumacher et al.

CHEMICAL COMMUNICATIONS (2018)

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Review Chemistry, Multidisciplinary

Principles and applications of EPR spectroscopy in the chemical sciences

Maxie M. Roessler et al.

CHEMICAL SOCIETY REVIEWS (2018)

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Review Chemistry, Multidisciplinary

From Synthesis of Amino Acids and Peptides to Enzymatic Catalysis: A Bottom-Up Approach in Mechanochemistry

Carsten Bolm et al.

CHEMSUSCHEM (2018)

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Article Chemistry, Multidisciplinary

Elusive Nonsolvated Cocrystals of Aspirin: Two Polymorphs with Bipyridine Discovered with the Assistance of Mechanochemistry

Shalisa M. Oburn et al.

CRYSTAL GROWTH & DESIGN (2018)

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Article Chemistry, Multidisciplinary

Mechanochemical syntheses and Cl-35 solid-state NMR characterization of fluoxetine HCl cocrystals

Austin A. Peach et al.

CRYSTENGCOMM (2018)

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Review Chemistry, Multidisciplinary

Mechanochemistry and organic synthesis: from mystical to practical

J. Andersen et al.

GREEN CHEMISTRY (2018)

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Article Biochemical Research Methods

1H line width dependence on MAS speed in solid state NMR - Comparison of experiment and simulation

Ulrich Sternberg et al.

JOURNAL OF MAGNETIC RESONANCE (2018)

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Article Chemistry, Physical

Mechanochemistry of the LiBH4-AlCl3 System: Structural Characterization of the Products by Solid-State NMR

T. Kobayashi et al.

JOURNAL OF PHYSICAL CHEMISTRY C (2018)

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Article Chemistry, Organic

Mechanochemical Organic Synthesis: The Art of Making Chemistry Green

Vjekoslav Strukil

SYNLETT (2018)

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Article Chemistry, Multidisciplinary

Mechanochemistry as an emerging tool for molecular synthesis: what can it offer?

Joseph L. Howard et al.

CHEMICAL SCIENCE (2018)

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Article Multidisciplinary Sciences

Magic angle spinning spheres

Pinhui Chen et al.

SCIENCE ADVANCES (2018)

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Article Medicine, Research & Experimental

In Situ Stimulated Raman Scattering (SRS) Microscopy Study of the Dissolution of Sustained-Release Implant Formulation

Andrew T. Francis et al.

MOLECULAR PHARMACEUTICS (2018)

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Article Chemistry, Multidisciplinary

Mechanochemistry: A Force of Synthesis

Jean-Louis Do et al.

ACS CENTRAL SCIENCE (2017)

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Article Chemistry, Organic

Altering Product Selectivity by Mechanochemistry

Jose G. Hernandez et al.

JOURNAL OF ORGANIC CHEMISTRY (2017)

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Correction Medicine, Research & Experimental

Characterization of the Particle Size and Polydispersity of Dicumarol Using Solid-State NMR Spectroscopy (vol 14, pg 856, 2017)

Kassibla Elodie Dempah et al.

MOLECULAR PHARMACEUTICS (2017)

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Article Chemistry, Organic

Approach toward the Understanding of Coupling Mechanism for EDC Reagent in Solvent-Free Mechanosynthesis

Aneta Wroblewska et al.

ORGANIC LETTERS (2017)

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Article Multidisciplinary Sciences

Local Structure of Ion Pair Interaction in Lapatinib Amorphous Dispersions characterized by Synchrotron X-Ray diffraction and Pair Distribution Function Analysis

Gabriel L. B. de Araujo et al.

SCIENTIFIC REPORTS (2017)

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Article Chemistry, Analytical

Innovative in Situ Ball Mill for X-ray Diffraction

Voraksmy Ban et al.

ANALYTICAL CHEMISTRY (2017)

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Article Chemistry, Multidisciplinary

Tandem In Situ Monitoring for Quantitative Assessment of Mechanochemical Reactions Involving Structurally Unknown Phases

Stipe Lukin et al.

CHEMISTRY-A EUROPEAN JOURNAL (2017)

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Article Chemistry, Multidisciplinary

A kinetic study of mechanochemical halogen bond formation by in situ 31P solid-state NMR spectroscopy

Yijue Xu et al.

CHEMICAL COMMUNICATIONS (2017)

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Review Pharmacology & Pharmacy

Screening for new pharmaceutical solid forms using mechanochemistry: A practical guide

Dritan Hasa et al.

ADVANCED DRUG DELIVERY REVIEWS (2017)

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Article Chemistry, Multidisciplinary

Knowing When To Stop-Trapping Metastable Polymorphs in Mechanochemical Reactions

Hannes Kulla et al.

CRYSTAL GROWTH & DESIGN (2017)

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Review Pharmacology & Pharmacy

Perspectives on the amorphisation/milling relationship in pharmaceutical materials

M. Descamps et al.

ADVANCED DRUG DELIVERY REVIEWS (2016)

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Article Chemistry, Multidisciplinary

Combining solid-state NMR spectroscopy with first-principles calculations - a guide to NMR crystallography

Sharon E. Ashbrook et al.

CHEMICAL COMMUNICATIONS (2016)

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Review Chemistry, Multidisciplinary

Advances in Quantum Mechanochemistry: Electronic Structure Methods and Force Analysis

Tim Stauch et al.

CHEMICAL REVIEWS (2016)

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Article Chemistry, Multidisciplinary

Polymorphism of Mechanochemically Synthesized Cocrystals: A Case Study

Franziska Fischer et al.

CRYSTAL GROWTH & DESIGN (2016)

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Article Chemistry, Multidisciplinary

Mechanochemical Synthesis of Multicomponent Crystals: One Liquid for One Polymorph? A Myth to Dispel

Dritan Hasa et al.

CRYSTAL GROWTH & DESIGN (2016)

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Article Chemistry, Physical

Nuclear magnetic resonance studies of DNP-ready trehalose obtained by solid state mechanochemical amorphization

M. Filibian et al.

PHYSICAL CHEMISTRY CHEMICAL PHYSICS (2016)

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Article Chemistry, Multidisciplinary

Mechanophores with a Reversible Radical System and Freezing-Induced Mechanochemistry in Polymer Solutions and Gels

Keiichi Imato et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

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Article Chemistry, Multidisciplinary

Dynamic nuclear polarization of a glassy matrix prepared by solid state mechanochemical amorphization of crystalline substances

E. Elisei et al.

CHEMICAL COMMUNICATIONS (2015)

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Article Biochemical Research Methods

Spinning proteins, the faster, the better?

Anja Boeckmann et al.

JOURNAL OF MAGNETIC RESONANCE (2015)

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Article Chemistry, Multidisciplinary

Direct In Situ Investigation of Milling Reactions Using Combined X-ray Diffraction and Raman Spectroscopy

Lisa Batzdorf et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

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Article Physics, Atomic, Molecular & Chemical

EPR and Optical Studies of Fe3+-Doped Ca-Li Hydroxyapatite Nanopowder: Mechanochemical Synthesis

K. Ravindranadh et al.

APPLIED MAGNETIC RESONANCE (2015)

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Article Chemistry, Multidisciplinary

Laboratory Real-Time and In Situ Monitoring of Mechanochemical Milling Reactions by Raman Spectroscopy

Davor Gracin et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

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Article Chemistry, Multidisciplinary

Better understanding of mechanochemical reactions: Raman monitoring reveals surprisingly simple 'pseudo-fluid' model for a ball milling reaction

Xiaohe Ma et al.

CHEMICAL COMMUNICATIONS (2014)

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Article Chemistry, Inorganic & Nuclear

Polymorphism in P,P-[3]ferrocenophanes: insights from an NMR crystallographic approach

Thomas Wiegand et al.

DALTON TRANSACTIONS (2014)

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Article Chemistry, Physical

Quantitative in situ and real-time monitoring of mechanochemical reactions

Ivan Halasz et al.

FARADAY DISCUSSIONS (2014)

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Article Chemistry, Physical

Mechanochemistry and sonochemistry: concluding remarks

Kenneth S. Suslick

FARADAY DISCUSSIONS (2014)

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Article Chemistry, Multidisciplinary

Solvent-free mechanochemical synthesis of alane, AlH3: effect of pressure on the reaction pathway

S. Gupta et al.

GREEN CHEMISTRY (2014)

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Article Chemistry, Physical

Monitoring Cocrystal Formation via In Situ Solid-State NMR

Venkata S. Mandala et al.

JOURNAL OF PHYSICAL CHEMISTRY LETTERS (2014)

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Article Chemistry, Multidisciplinary

In Vivo Metabolic Fingerprinting of Neutral Lipids with Hyperspectral Stimulated Raman Scattering Microscopy

Dan Fu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

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Article Pharmacology & Pharmacy

Investigating Gabapentin Polymorphism Using Solid-State NMR Spectroscopy

Kassibla E. Dempah et al.

AAPS PHARMSCITECH (2013)

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Article Chemistry, Multidisciplinary

Real-Time In Situ Powder X-ray Diffraction Monitoring of Mechanochemical Synthesis of Pharmaceutical Cocrystals

Ivan Halasz et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

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Review Chemistry, Multidisciplinary

Mechanochemical preparation of co-crystals

Dario Braga et al.

CHEMICAL SOCIETY REVIEWS (2013)

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Review Chemistry, Multidisciplinary

The historical development of mechanochemistry

Laszlo Takacs

CHEMICAL SOCIETY REVIEWS (2013)

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Review Chemistry, Multidisciplinary

Mechanochemistry of inorganic and organic systems: what is similar, what is different?

Elena Boldyreva

CHEMICAL SOCIETY REVIEWS (2013)

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Article Chemistry, Multidisciplinary

Mechanochemical Conversions Between Crystalline Polymorphs of a Complex Organic Solid

Benjamin D. Altheimer et al.

CRYSTAL GROWTH & DESIGN (2013)

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Article Medicine, Research & Experimental

Probing Hydrogen Bonding in Cocrystals and Amorphous Dispersions Using 14N-1H HMQC Solid-State NMR

Andrew S. Tatton et al.

MOLECULAR PHARMACEUTICS (2013)

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Article Chemistry, Multidisciplinary

Real-time and in situ monitoring of mechanochemical milling reactions

Tomislav Friscic et al.

NATURE CHEMISTRY (2013)

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Article Biochemical Research Methods

In situ and real-time monitoring of mechanochemical milling reactions using synchrotron X-ray diffraction

Ivan Halasz et al.

NATURE PROTOCOLS (2013)

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Review Pharmacology & Pharmacy

The role of co-crystals in pharmaceutical design

Jonathan W. Steed

TRENDS IN PHARMACOLOGICAL SCIENCES (2013)

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Article Chemistry, Multidisciplinary

Identifying the intermolecular hydrogen-bonding supramolecular synthons in an indomethacin-nicotinamide cocrystal by solid-state NMR

Keisuke Maruyoshi et al.

CHEMICAL COMMUNICATIONS (2012)

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Review Chemistry, Multidisciplinary

First-Principles Calculation of NMR Parameters Using the Gauge Including Projector Augmented Wave Method: A Chemist's Point of View

Christian Bonhomme et al.

CHEMICAL REVIEWS (2012)

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Review Chemistry, Multidisciplinary

Supramolecular concepts and new techniques in mechanochemistry: cocrystals, cages, rotaxanes, open metal-organic frameworks

Tomislav Friscic

CHEMICAL SOCIETY REVIEWS (2012)

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Review Chemistry, Multidisciplinary

Mechanochemistry: opportunities for new and cleaner synthesis

Stuart L. James et al.

CHEMICAL SOCIETY REVIEWS (2012)

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Article Environmental Sciences

Mechanochemistry of ibuprofen pharmaceutical

Salvatore Andini et al.

CHEMOSPHERE (2012)

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Article Chemistry, Multidisciplinary

The role of mechanochemistry and supramolecular design in the development of pharmaceutical materials

Amit Delori et al.

CRYSTENGCOMM (2012)

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Article Chemistry, Physical

Applications of high-resolution 1H solid-state NMR

Steven P. Brown

SOLID STATE NUCLEAR MAGNETIC RESONANCE (2012)

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Article Chemistry, Physical

N-14-H-1 Heteronuclear Multiple-Quantum Correlation Magic-Angle Spinning NMR Spectroscopy of Organic Solids

Andrew S. Tatton et al.

ZEITSCHRIFT FUR PHYSIKALISCHE CHEMIE-INTERNATIONAL JOURNAL OF RESEARCH IN PHYSICAL CHEMISTRY & CHEMICAL PHYSICS (2012)

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Article Biochemical Research Methods

BaBa-xy16: Robust and broadband homonuclear DQ recoupling for applications in rigid and soft solids up to the highest MAS frequencies

Kay Saalwaechter et al.

JOURNAL OF MAGNETIC RESONANCE (2011)

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Article Chemistry, Physical

Solid State Mutarotation of Glucose

N. Dujardin et al.

JOURNAL OF PHYSICAL CHEMISTRY B (2011)

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Article Chemistry, Multidisciplinary

Direct observation of a transient polymorph during crystallization

Colan E. Hughes et al.

CHEMICAL COMMUNICATIONS (2010)

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Article Chemistry, Inorganic & Nuclear

Chirality-dependent sublimation of α-(trifluoromethyl)-lactic acid: Relative vapor pressures of racemic, eutectic, and enantiomerically pure forms, and vibrational spectroscopy of isolated (S,S) and (S,R) dimers

Merwe Albrecht et al.

JOURNAL OF FLUORINE CHEMISTRY (2010)

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Article Chemistry, Multidisciplinary

Ultrafast MAS Solid-State NMR Permits Extensive 13C and 1H Detection in Paramagnetic Metalloproteins

Ivano Bertini et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2010)

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Review Chemistry, Physical

Indirect detection of nitrogen-14 in solid-state NMR spectroscopy

Simone Cavadini

PROGRESS IN NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY (2010)

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Article Chemistry, Multidisciplinary

Solid-State NMR Analysis of Organic Cocrystals and Complexes

Frederick G. Vogt et al.

CRYSTAL GROWTH & DESIGN (2009)

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Article Chemistry, Multidisciplinary

Rapid analysis of organic compounds by proton-detected heteronuclear correlation NMR spectroscopy with 40 kHz magic-angle spinning

Donghua H. Zhou et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2008)

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Letter Chemistry, Physical

A technique for in situ monitoring of crystallization from solution by solid-state 13C CPMAS NMR spectroscopy

Colan E. Hughes et al.

JOURNAL OF PHYSICAL CHEMISTRY A (2008)

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Article Physics, Condensed Matter

Solid state vitrification of crystalline α and β-D-glucose by mechanical milling

N. Dujardin et al.

SOLID STATE COMMUNICATIONS (2008)

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Article Chemistry, Multidisciplinary

Phenomenon of optical self-purification of chiral non-racemic compounds

Vadim A. Soloshonok et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2007)

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Review Chemistry, Physical

Probing proton-proton proximities in the solid state

Steven P. Brown

PROGRESS IN NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY (2007)

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Article Chemistry, Medicinal

Investigation of the effects of pharmaceutical processing upon solid-state NMR relaxation times and implications to solid-state formulation stability

Joseph W. Lubach et al.

JOURNAL OF PHARMACEUTICAL SCIENCES (2007)

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Article Chemistry, Physical

Bulk chemical shifts in hydrogen-bonded systems from first-principles calculations and solid-state-NMR

J. Schmidt et al.

JOURNAL OF PHYSICAL CHEMISTRY B (2006)

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Article Biochemical Research Methods

Indirect detection of nitrogen-14 in solids via protons by nuclear magnetic resonance spectroscopy

Simone Cavadini et al.

JOURNAL OF MAGNETIC RESONANCE (2006)

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Article Chemistry, Multidisciplinary

An investigation of weak CH•••O hydrogen bonds in maltose anomers by a combination of calculation and experimental solid-state NMR spectroscopy

JR Yates et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2005)

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Article Chemistry, Multidisciplinary

Solid-phase mechanochemical incorporation of a spin label into cellulose

AV Dushkin et al.

RUSSIAN CHEMICAL BULLETIN (2005)

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Article Chemistry, Inorganic & Nuclear

NMR crystallography: the use of chemical shifts

RK Harris

SOLID STATE SCIENCES (2004)

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Article Pharmacology & Pharmacy

Solid state NMR and DSC methods for quantifying the amorphous content in solid dosage forms:: an application to ball-milling of trehalose

R Lefort et al.

INTERNATIONAL JOURNAL OF PHARMACEUTICS (2004)

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Article Chemistry, Multidisciplinary

Refinement of hydrogen atomic position in a hydrogen bond using a combination of solid-state NMR and computation

RK Harris et al.

CHEMICAL COMMUNICATIONS (2003)

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Article Spectroscopy

Modification of kaolinite surfaces through mechanochemical treatment -: a mid-IR and near-IR spectroscopic study

RL Frost et al.

SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY (2002)

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Article Chemistry, Physical

Effects of polymorphism on functional group dynamics:: Solid state 2H NMR studies of the dynamic properties of the α and β phases of L-glutamic acid

SJ Kitchin et al.

JOURNAL OF PHYSICAL CHEMISTRY A (2002)

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Article Chemistry, Multidisciplinary

Mechanochemistry and co-crystal formation: effect of solvent on reaction kinetics

N Shan et al.

CHEMICAL COMMUNICATIONS (2002)

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Article Chemistry, Multidisciplinary

Solvent-free mechanochemical synthesis of phosphonium salts

VP Balema et al.

CHEMICAL COMMUNICATIONS (2002)

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Article Chemistry, Multidisciplinary

Solvent-free mechanochemical synthesis of two Pt complexes: cis-(Ph3P)(2)PtCl2 and cis-(Ph3P)(2)PtCO3

VP Balema et al.

CHEMICAL COMMUNICATIONS (2002)

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Article Engineering, Chemical

Mechanism and kinetics of mechanochemical processes in comminuting devices - 1. Theory

FK Urakaev et al.

POWDER TECHNOLOGY (2000)

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Article Materials Science, Multidisciplinary

Quicksilver from Cinnabar: The first documented mechanochemical reaction?

L Takacs

JOM-JOURNAL OF THE MINERALS METALS & MATERIALS SOCIETY (2000)

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