Interpretation of Organic Spectra


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NMR Spectroscopy [nuclear magnetic resonance] ; Basic principle & Interpretation of organic spectra

Skickas inom vardagar. Although there are a number of books in this field, most of them lack an introduction of comprehensive analysis of MS and IR spectra, and others do not provide up-to-date information like tandem MS. This book fills the gap.

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The energy of the electron beam is typically 70 electronvolts and the ionization process typically produces extensive fragmentation of the chemical bonds of the molecule. Once the fragmentation is initiated, the electron is first excited from the site with the lowest ionization energy. The peak in the mass spectrum with the greatest intensity is called the base peak. The peak corresponding to the molecular ion is often, but not always, the base peak. Identification of the molecular ion can be difficult.

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Examining organic compounds, the relative intensity of the molecular ion peak diminishes with branching and with increasing mass in a homologous series. Molecular ion peaks are also often preceded by an M-1 or M-2 peak resulting from loss of a hydrogen radical or dihydrogen. Peaks with mass less than the molecular ion are the result of fragmentation of the molecule.

Many reaction pathways exist for fragmentation, but only newly formed cations will show up in the mass spectrum, not radical fragments or neutral fragments. Metastable peaks are broad peaks with low intensity at non-integer mass values. These peaks result from ions with lifetimes shorter than the time needed to traverse the distance between ionization chamber and the detector.

Infrared Spectroscopy: A Quick Primer On Interpreting Spectra

The nitrogen rule states that organic molecules that contain hydrogen , carbon , nitrogen , oxygen , silicon , phosphorus , sulfur , and the halogens have an odd nominal mass if they have an odd number of nitrogen atoms or an even mass if they have an even number of nitrogen atoms are present. From degree of unsaturation principles, molecules containing only carbon, hydrogen, halogens, nitrogen, and oxygen follow the formula. The even electron rule states that ions with an even number of electrons cations but not radical ions tend to form even-electron fragment ions and odd-electron ions radical ions form odd-electron ions or even-electron ions.

The more stable the product cation, the more abundant the corresponding decomposition process. Several theories can be utilized to predict the fragmentation process, such as the electron octet rule, the resonance stabilization and hyperconjugation and so on. The Rule of 13 is a simple procedure for tabulating possible chemical formula for a given molecular mass.

If the molecular weight of the molecule in question is M , the number of possible CH units is n and.


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A negative value of u indicates the presence of heteroatoms in the molecule and a half-integer value of u indicates the presence of an odd number of nitrogen atoms. On addition of heteroatoms, the molecular formula is adjusted by the equivalent mass of carbon and hydrogen. Isotope peaks within a spectrum can help in structure elucidation. Compounds containing halogens especially chlorine and bromine can produce very distinct isotope peaks. Even when compounds only contain elements with less intense isotope peaks carbon or oxygen , the distribution of these peaks can be used to assign the spectrum to the correct compound.

The fragmentation pattern of the spectra beside the determination of the molar weight of an unknown compound also suitable to give structural information, especially in combination with the calculation of the degree of unsaturation from the molecular formula when available. Neutral fragments frequently lost are carbon monoxide , ethylene , water , ammonia , and hydrogen sulfide.

There are several fragmentation processes, as follows. Fragmentation arises from a homolysis processes. This cleavage results from the tendency of the unpaired electron from the radical site to pair up with an electron from another bond to an atom adjacent to the charge site, as illustrated below. In this depiction, single-electron movements are indicated by a single-headed arrow.

The ionization of alkanes weakens the C-C bond, ultimately resulting in the decomposition. Highly substituted carbocations are more stable than the nonsubstituted ones. An example is depicted as below. This reaction results from the inductive effect of the radical sites, as depicted below. This reaction is defined as a heterolytic cleavage since a pair of electrons is transferred.

The same requirements for McLafferty rearrangement apply to hydrogen rearrangement to a saturated heteroatom. Such rearrangement initiates charge-site reaction, resulting in the formation of an odd electron ion and a small neutral molecule water, or acid and so on. For alcohols, this heterolytic cleavage releases a water molecule. The same requirements for McLafferty rearrangement apply to double-hydrogen rearrangement. This reaction is observed for three unsaturated functional groups, namely thioesters, esters and amides.

Such rearrangement initiates charge-site reaction, resulting in the formation of an odd electron ion and a small neutral molecule water, or HCl and so on.

Interpretation of Organic Spectra - Yong-Cheng Ning - Bok () | Bokus

This reaction can be utilized to differentiate ortho from para and meta isomersMcLafferty rearrangement apply to double-hydrogen rearrangement. This reaction occurs mainly in cyclohexene and its derivatives. Upon ionization, the pi electrons are excited and generate a charge site and a radical site. This reaction occurs mainly in four-membered cyclic molecules. Once ionized, it produces a distonic ion and then further fragments to yield an ethene radical ion and a neutral ethene molecule. For linear alkanes, molecular ion peaks are often observed. However, for long chain compounds, the intensity of the molecular ion peaks are often weak.

For example, hexane fragmentation patterns. Branched alkanes have somewhat weaker molecular ion peaks in the spectra. They tend to fragment at the branched point. Cycloalkanes have relatively intense molecular ion peaks two bonds have to break. Alkene fragmentation peaks are often most significant mode. However, for the substituted cycloalkanes, they prefer to form the cycloalkyl cations by cleavage at the branched points. After the ionization, double bonds can migrate easily, resulting in almost impossible determination of isomers. Allylic cleavage is most significant fragmentation mode due to resonance stabilization.


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McLafferty-like rearrangements are possible similar to carbonyl pi bonds.

Interpretation of Organic Spectra Interpretation of Organic Spectra
Interpretation of Organic Spectra Interpretation of Organic Spectra
Interpretation of Organic Spectra Interpretation of Organic Spectra
Interpretation of Organic Spectra Interpretation of Organic Spectra
Interpretation of Organic Spectra Interpretation of Organic Spectra
Interpretation of Organic Spectra Interpretation of Organic Spectra
Interpretation of Organic Spectra Interpretation of Organic Spectra

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