Bird-in-the-Hand Method for Determination of Absolute Configuration in Fischer Projections

Siloac, Edward

doi:10.1021/ed076p798

Cited by 9 publications

(8 citation statements)

References 12 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The conversion of Fischer into zig-zag projections has been reported previously [1]. However, when it comes to visualization, students will find the model described here easier to understand 1 .…”

Section: Interconversion Of Fischer and Zig-zag Projectionsmentioning

confidence: 78%

“…The use of hands has been shown to be effective in the three-dimensional visualization of molecules [1]. A method of looking at one's own hands as a model that allows students to see the interconversion of Fischer and zig-zag projections is described in this article.…”

Section: Interconversion Of Fischer and Zig-zag Projectionsmentioning

confidence: 99%

“…RESONANCE¨April 2010 1 A common misconception about the conversion of a Fischer to zig-zag projection is that the placement of two adjacent groups (on the same side of the Fischer projection) to the opposite sides of the zig-zag backbone can provide the correct zig-zag structure. This is true only if we are concerned with the relative stereochemistry.…”

mentioning

confidence: 99%

See 2 more Smart Citations

Interconversion of Fischer and zig-zag projections learning stereochemistry with the help of hands

Hussaini

2010

Reson

View full text Add to dashboard Cite

1 A common misconception about the conversion of a Fischer to zig-zag projection is that the placement of two adjacent groups (on the same side of the Fischer projection) to the opposite sides of the zig-zag backbone can provide the correct zig-zag structure. This is true only if we are concerned with the relative stereochemistry. The author's method is suitable for the correct representation of absolute stereochemistry as well. KeywordsStereochemistry, conformational analysis, hands-on learning, Fischer projections, zig-zag projection, C-C bond rotations. Interconversion of Fischer and Zig-Zag ProjectionsLearning Stereochemistry with the Help of Hands Visualization of molecules in three dimensions is an important aspect of organic chemistry. The use of hands has been shown to be effective in the three-dimensional visualization of molecules [1]. A method of looking at one's own hands as a model that allows students to see the interconversion of Fischer and zig-zag projections is described in this article.IUPAC has defined a zig-zag projection as "a stereochemical projection for an acyclic molecule (or portion of a molecule) where the main chain is represented by a zig-zag line in the plane and the substituents are shown above or below the plane" [2]. Other, less correct names, such as skeletal structure and flying wedge formula are also common for the same projection.The conversion of Fischer into zig-zag projections has been reported previously [1]. However, when it comes to visualization, students will find the model described here easier to understand 1 . The method follows as below.Consider the Fischer projection (1) (Scheme 1).

show abstract

Section: Interconversion Of Fischer and Zig-zag Projectionsmentioning

confidence: 78%

Section: Interconversion Of Fischer and Zig-zag Projectionsmentioning

confidence: 99%

See 1 more Smart Citation

Interconversion of Fischer and zig-zag projections learning stereochemistry with the help of hands

Hussaini

2010

Reson

View full text Add to dashboard Cite

show abstract

“…It also has limited utility for the new student who just needs a simple model that can be understood and retained without reference to external objects like 3-D models or flowcharts. With regard to organic chemistry (where the assignment of R or S to enantiomers of tetrahedral carbon chiral centers requires the ranking of ligands according to CIP rules), the clocking model presented here is a lead-in to this topic, which has been thoroughly covered in previous publications. − The general chemistry student is alerted to the importance of chirality to chemistry, that it has consequences for molecular function, and that it is not just an abstraction relating structure to geometry. Here, a general method of determining chirality for the tetrahedral structures important to organic chemistry, as well as for the square planar and octahedral structures more commonly encountered in inorganic chemistry, is presented.…”

Section: Introductionmentioning

confidence: 99%

Clock It: Solving the 3-D Chirality Problem with a 2-D Method—A Simple Algorithm for Teaching and Determining Enantiomers in General Chemistry

Juszczak

2021

J. Chem. Educ.

View full text Add to dashboard Cite

One of the more difficult concepts introduced in the first-year undergraduate course, general chemistry, is that of chirality. Typically, left and right hands are the common, macroscopic objects of reference used to demonstrate the quality of being nonsuperimposable, followed by the use of a mirror and molecular models, to illustrate molecular enantiomers. While this approach works well as an introduction, and the handedness model becomes more useful in organic chemistry where absolute R- and S-configuration assignment becomes necessary, it does not help the general chemistry student to determine molecular chirality or “handedness” at this basic level. Much of the difficulty stems from the representation of 3-dimensional (3-D) structures on the 2-dimensional (2-D) paper plane. While detailed flowcharts exist for molecules of varying orbital hybridization and geometry, these are more suited to advanced students in inorganic chemistry and are not designed to be mentally retained or learned. Additionally, the process of determining R- and S-configurations for carbon tetrahedral centers in organic chemistry is more complex as ligands must be ranked according to Cahn–Ingold–Prelog (CIP) rules. Previous publications have addressed this topic thoroughly. A simple method is presented here (called clocking) which introduces the concept of chirality for general chemistry and primes the way for more complex chirality assignments in higher level courses.

show abstract

“…Nobel Laureate Emil Fischer developed his namesake projections during his study of carbohydrates to aid in the structural analyses of stereoisomeric sugars. , His contribution to organic chemistry is still taught in classrooms around the world, through Fischer projections, enabling students to explore countless classes of organic compounds via conformational analysis and stereochemistry. − There are a plethora of publications regarding methodologies that use these projections, which represent a molecule in an entirely eclipsed conformation, to assign ( R )- or ( S )-configurations to stereogenic centers. − Several articles have also been published describing the interconversion of Fischer and Haworth projections. − However, the literature is less abundant in articles highlighting the conversion of Fischer projections into bond-line representations, , or the inverse transformation , to be discussed herein.…”

Section: Introductionmentioning

confidence: 99%

Conformational Tug of War: A Technique for Converting Bond-Line Structures into Fischer Projections

Butler

2020

J. Chem. Educ.

View full text Add to dashboard Cite

Undergraduate organic chemistry students, as they study conformational analysis and stereochemistry, frequently have trouble manipulating three-dimensional structures on a two-dimensional page or screen. The inability to accurately convert three-dimensional bond-line representations into Fischer projections is one example of this. While some students can utilize traditional approaches, other students require another way to visualize the molecule in order to perform the conversion. This text describes a method for converting bond-line structures of varying chain lengths and conformations into corresponding Fischer projections.

show abstract

Bird-in-the-Hand Method for Determination of Absolute Configuration in Fischer Projections

Cited by 9 publications

References 12 publications

Interconversion of Fischer and zig-zag projections learning stereochemistry with the help of hands

Interconversion of Fischer and zig-zag projections learning stereochemistry with the help of hands

Clock It: Solving the 3-D Chirality Problem with a 2-D Method—A Simple Algorithm for Teaching and Determining Enantiomers in General Chemistry

Conformational Tug of War: A Technique for Converting Bond-Line Structures into Fischer Projections

Contact Info

Product

Resources

About